Photoinduced oxidation of an indole derivative: 2-(1′ H -indol-2′-yl)-[1,5]naphthyridine

Golec, Barbara; Nawara, Krzysztof; Thummel, Randolph P.; Waluk, Jacek

doi:10.1039/C8PP00587G

Title: Photoinduced oxidation of an indole derivative: 2-(1′ H -indol-2′-yl)-[1,5]naphthyridine

Abstract

UV-induced photooxidation of a 2-substituted indole derivative provides an efficient way for the formation of a benzoxazinone derivative.

Authors:

^[1];

^[2];

^[3];

^[4]

Institute of Physical Chemistry, Polish Academy of Sciences, 01-224 Warsaw, Poland
Faculty of Mathematics and Science, Cardinal Stefan Wyszyński University, 01-815 Warsaw, Poland
Department of Chemistry, University of Houston, Houston, USA
Institute of Physical Chemistry, Polish Academy of Sciences, 01-224 Warsaw, Poland, Faculty of Mathematics and Science

Publication Date:: 2019-09-11

Sponsoring Org.:: USDOE Office of Science (SC), Basic Energy Sciences (BES)

OSTI Identifier:: 1502271

Grant/Contract Number:: FG02-07ER15888

Resource Type:: Publisher's Accepted Manuscript

Journal Name:: Photochemical & Photobiological Sciences

Additional Journal Information:: Journal Name: Photochemical & Photobiological Sciences Journal Volume: 18 Journal Issue: 9; Journal ID: ISSN 1474-905X

Publisher:: Royal Society of Chemistry (RSC)

Country of Publication:: United Kingdom

Language:: English

Citation Formats


                    Golec, Barbara, Nawara, Krzysztof, Thummel, Randolph P., and Waluk, Jacek. Photoinduced oxidation of an indole derivative: 2-(1′ H -indol-2′-yl)-[1,5]naphthyridine.  United Kingdom: N. p., 2019. 
Web.  doi:10.1039/C8PP00587G.

Copy to clipboard


                    Golec, Barbara, Nawara, Krzysztof, Thummel, Randolph P., & Waluk, Jacek. Photoinduced oxidation of an indole derivative: 2-(1′ H -indol-2′-yl)-[1,5]naphthyridine.  United Kingdom.  https://doi.org/10.1039/C8PP00587G

Copy to clipboard


                    Golec, Barbara, Nawara, Krzysztof, Thummel, Randolph P., and Waluk, Jacek. Wed .  
"Photoinduced oxidation of an indole derivative: 2-(1′ H -indol-2′-yl)-[1,5]naphthyridine".  United Kingdom.  https://doi.org/10.1039/C8PP00587G.

Copy to clipboard


                    
@article{osti_1502271,

  title        = {Photoinduced oxidation of an indole derivative: 2-(1′ H -indol-2′-yl)-[1,5]naphthyridine},

  author       = {Golec, Barbara and Nawara, Krzysztof and Thummel, Randolph P. and Waluk, Jacek},

  abstractNote = {UV-induced photooxidation of a 2-substituted indole derivative provides an efficient way for the formation of a benzoxazinone derivative.},

  doi          = {10.1039/C8PP00587G},

  journal      = {Photochemical & Photobiological Sciences},

  number       = 9,

  volume       = 18,

  place        = {United Kingdom},

  year         = {2019},

  month        = {9}

}

Copy to clipboard

Journal Article:

Free Publicly Available Full Text

Accepted Manuscript (Publisher)

Publisher's Version of Record
https://doi.org/10.1039/C8PP00587G

Other availability

Search WorldCat to find libraries that may hold this journal

Citation Metrics:

Cited by: 3 works

Citation information provided by
Web of Science

Save / Share:

Export Metadata

Save to My Library

Works referenced in this record:

Oxidation of 2-arylindoles for synthesis of 2-arylbenzoxazinones with oxone as the sole oxidant
journal, January 2013

Lian, Xiao-Li; Lei, Hao; Quan, Xue-Jing
Chemical Communications, Vol. 49, Issue 74
DOI: 10.1039/c3cc44215b

1,4-Benzothiazine and 1,4-Benzoxazine imidazole derivatives with antifungal activity: A docking study
journal, November 2002

Macchiarulo, Antonio; Costantino, Gabriele; Fringuelli, Daniele
Bioorganic & Medicinal Chemistry, Vol. 10, Issue 11
DOI: 10.1016/S0968-0896(02)00263-8

Light emission from tryptophan oxidation by hypobromous acid: Light emission from tryptophan oxidation by hypobromous acid
journal, October 2012

Petrônio, Maicon Segalla; Ximenes, Valdecir Farias
Luminescence, Vol. 28, Issue 6
DOI: 10.1002/bio.2445

Studies on Some Benzoxazine-4-one Derivatives with Potential Biological Activity
journal, May 2012

M. O. Habib, Osman; M. Hassan, Ahmed El-Meka, Hussein
American Journal of Organic Chemistry, Vol. 2, Issue 3
DOI: 10.5923/j.ajoc.20120203.02

Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density
journal, January 1988

Lee, Chengteh; Yang, Weitao; Parr, Robert G.
Physical Review B, Vol. 37, Issue 2
DOI: 10.1103/PhysRevB.37.785

Copper-mediated oxidative tandem reactions with molecular oxygen: synthesis of 2-arylbenzoxazinone derivatives from indoles
journal, April 2014

Yamashita, Mitsuaki; Iida, Akira
Tetrahedron Letters, Vol. 55, Issue 18
DOI: 10.1016/j.tetlet.2014.03.128

Synthesis of Isatins by I ₂ /TBHP Mediated Oxidation of Indoles
journal, May 2014

Zi, You; Cai, Zhong-Jian; Wang, Shun-Yi
Organic Letters, Vol. 16, Issue 11
DOI: 10.1021/ol501203q

Density-functional exchange-energy approximation with correct asymptotic behavior
journal, September 1988

Becke, A. D.
Physical Review A, Vol. 38, Issue 6
DOI: 10.1103/PhysRevA.38.3098

Protect from Light: Photodegradation and Protein Biologics
journal, June 2007

Kerwin, Bruce A.; Remmele, Richard L.
Journal of Pharmaceutical Sciences, Vol. 96, Issue 6
DOI: 10.1002/jps.20815

Dissociative Excitation Energy Transfer in the Reactions of Protonated Cysteine and Tryptophan with Electronically Excited Singlet Molecular Oxygen (a ¹ Δ _g )
journal, August 2011

Liu, Fangwei; Fang, Yigang; Chen, Yun
The Journal of Physical Chemistry B, Vol. 115, Issue 32
DOI: 10.1021/jp205235d

Synthesis of 2-Oxindoles from Substituted Indoles by Hypervalent-Iodine Oxidation: Synthesis of 2-Oxindoles from Substituted Indoles by Hypervalent-Iodine Oxidation
journal, March 2018

Jiang, Xinpeng; Zheng, Cong; Lei, Lijun
European Journal of Organic Chemistry, Vol. 2018, Issue 12
DOI: 10.1002/ejoc.201701807

Structure and Photophysics of 2-(2‘-Pyridyl)benzindoles: The Role of Intermolecular Hydrogen Bonds
journal, November 2007

Petkova, Irina; Mudadu, Maria S.; Singh, Ajay
The Journal of Physical Chemistry A, Vol. 111, Issue 45
DOI: 10.1021/jp0735841

The Photophysics and Photochemistry of the Near-Uv Absorbing Amino Acids-I. Tryptophan and its Simple Derivatives
journal, April 1984

Creed, David
Photochemistry and Photobiology, Vol. 39, Issue 4
DOI: 10.1111/j.1751-1097.1984.tb03890.x

Altering the regioselectivity of cytochrome P450 BM-3 by saturation mutagenesis for the biosynthesis of indirubin
journal, November 2010

Hu, Sheng; Huang, Jun; Mei, Lehe
Journal of Molecular Catalysis B: Enzymatic, Vol. 67, Issue 1-2
DOI: 10.1016/j.molcatb.2010.07.001

Light-Induced Oxidation of Tryptophan and Histidine. Reactivity of Aromatic N -Heterocycles toward Triplet-Excited Flavins
journal, June 2009

Huvaere, Kevin; Skibsted, Leif H.
Journal of the American Chemical Society, Vol. 131, Issue 23
DOI: 10.1021/ja809039u

Temperature dependent steric hindrance effects in triplet state relaxation of meso-phenyl-substituted Pd-octaethylporphyrins
journal, March 2018

Gorski, Alexandr; Knyukshto, Valery; Zenkevich, Eduard
Journal of Photochemistry and Photobiology A: Chemistry, Vol. 354
DOI: 10.1016/j.jphotochem.2017.09.002

Expansion of Substrate Specificity of Cytochrome P450 2A6 by Random and Site-directed Mutagenesis
journal, October 2005

Wu, Zhong-Liu; Podust, Larissa M.; Guengerich, F. Peter
Journal of Biological Chemistry, Vol. 280, Issue 49
DOI: 10.1074/jbc.M508182200

Tryptophan oxidation photosensitized by pterin
journal, October 2013

Thomas, Andrés H.; Serrano, Mariana P.; Rahal, Virginie
Free Radical Biology and Medicine, Vol. 63
DOI: 10.1016/j.freeradbiomed.2013.05.044

The photochemistry of indomethacin
journal, September 1991

Weedon, Alan C.; Wong, David F.
Journal of Photochemistry and Photobiology A: Chemistry, Vol. 61, Issue 1
DOI: 10.1016/1010-6030(91)85071-N

Synthesis and evaluation of condensed and noncondensed heterocyclic compounds of industrial application
journal, September 2006

Eissa, A. M. F.; El-Sayed, R.
Journal of Heterocyclic Chemistry, Vol. 43, Issue 5
DOI: 10.1002/jhet.5570430505

Inhibition of human chymase by 2-amino-3,1-benzoxazin-4-ones
journal, April 2001

Neumann, Ulf; Schechter, Norman M.; Gütschow, Michael
Bioorganic & Medicinal Chemistry, Vol. 9, Issue 4
DOI: 10.1016/S0968-0896(00)00310-2

Photooxidation of Tryptophan and Tyrosine Residues in Human Serum Albumin Sensitized by Pterin: A Model for Globular Protein Photodamage in Skin
journal, August 2016

Reid, Lara O.; Roman, Ernesto A.; Thomas, Andrés H.
Biochemistry, Vol. 55, Issue 34
DOI: 10.1021/acs.biochem.6b00420

Solvent-Induced Changes in Photophysics and Photostability of Indole-Naphthyridines
journal, December 2014

Golec, Barbara; Kijak, Michał; Vetokhina, Volha
The Journal of Physical Chemistry B, Vol. 119, Issue 24
DOI: 10.1021/jp510846w

Irreversible Inhibitors of Serine, Cysteine, and Threonine Proteases
journal, December 2002

Powers, James C.; Asgian, Juliana L.; Ekici, Özlem Doǧan
Chemical Reviews, Vol. 102, Issue 12
DOI: 10.1021/cr010182v

Rotational isomerism in trans-1,2-diarylethylenes
journal, December 1991

Mazzucato, Ugo.; Momicchioli, Fabio.
Chemical Reviews, Vol. 91, Issue 8
DOI: 10.1021/cr00008a002

Optimization of bio-indigo production by recombinant E. coli harboring fmo gene
journal, June 2008

Han, Gui Hwan; Shin, Hyun-Jae; Kim, Si Wouk
Enzyme and Microbial Technology, Vol. 42, Issue 7
DOI: 10.1016/j.enzmictec.2008.02.004

Synthesis and evaluation of benzoxazinone derivatives on activity of human neutrophil elastase and on hemorrhagic shock-induced lung injury in rats
journal, July 2010

Hsieh, Pei-Wen; Yu, Huang-Ping; Chang, Yi-Ju
European Journal of Medicinal Chemistry, Vol. 45, Issue 7
DOI: 10.1016/j.ejmech.2010.03.046

Solvent-Induced s yn − a nti Rotamerization of 2-(2‘-Pyridyl)indole and the Structure of its Alcohol Complexes
journal, March 2000

Kyrychenko, A.; Herbich, J.; Wu, F.
Journal of the American Chemical Society, Vol. 122, Issue 12
DOI: 10.1021/ja991818r

Expression of naphthalene oxidation genes in Escherichia coli results in the biosynthesis of indigo
journal, October 1983

Ensley, B.; Ratzkin, B.; Osslund, T.
Science, Vol. 222, Issue 4620
DOI: 10.1126/science.6353574

New method for the synthesis of 3(2H)-pyridazinones and their alkene precursors: Solvent-free reactions under microwave irradiation
journal, September 1995

Jolivet, Sandrine; Texier-Boullet, Fran�oise; Hamelin, Jack
Heteroatom Chemistry, Vol. 6, Issue 5
DOI: 10.1002/hc.520060512

Mechanism for slow-binding inhibition of human leukocyte elastase by valine-derived benzoxazinones
journal, June 1987

Stein, Ross L.; Strimpler, Ann M.; Viscarello, Barbara R.
Biochemistry, Vol. 26, Issue 13
DOI: 10.1021/bi00387a057

The Witkop-Winterfeldt-Oxidation of Indoles
journal, January 2007

Mentel, Matthias; Breinbauer, Rolf
Current Organic Chemistry, Vol. 11, Issue 2
DOI: 10.2174/138527207779316426

Geometric isomerism in the phenylhydrazones of some .alpha.-dicarbonyl compounds
journal, March 1978

Yoder, Claude H.; Kennedy, Steven; Snavely, Fred A.
The Journal of Organic Chemistry, Vol. 43, Issue 6
DOI: 10.1021/jo00400a010

Photooxygenation of Heterocycles
journal, January 2005

Iesce, M.; Cermola, Flavio; Temussi, Fabio
Current Organic Chemistry, Vol. 9, Issue 2
DOI: 10.2174/1385272053369222

Construction of Metabolic Operons Catalyzing the De Novo Biosynthesis of Indigo in Escherichia coli
journal, March 1993

Murdock, Douglas; Ensley, Burt D.; Serdar, Cuneyt
Bio/Technology, Vol. 11, Issue 3
DOI: 10.1038/nbt0393-381

Photooxidation of Tryptophan Leading to 2-Aminoacetophenone - A Possible Reason for the Untypical Aging Off-flavor in Wine
journal, August 2014

Horlacher, Nora; Schwack, Wolfgang
Photochemistry and Photobiology, Vol. 90, Issue 6
DOI: 10.1111/php.12321

Combined effect of hydrogen bonding interactions and freezing of rotameric equilibrium on the enhancement of photostability
journal, January 2018

Golec, Barbara; Nawara, Krzysztof; Gorski, Alexandr
Physical Chemistry Chemical Physics, Vol. 20, Issue 19
DOI: 10.1039/C8CP00726H

Phenyl-substituted porphyrins. 1. Synthesis of meso-phenyl-substituted porphyrins
journal, October 2004

Syrbu, S. A.; Lyubimova, T. V.; Semeikin, A. S.
Chemistry of Heterocyclic Compounds, Vol. 40, Issue 10
DOI: 10.1007/s10593-005-0050-6

Investigation on the phototransformation of tadalafil in aqueous media. 6-Epimerization vs. solvent trapping reaction
journal, January 2010

Temussi, Fabio; Bassolino, Giovanni; Cermola, Flavio
Photochemical & Photobiological Sciences, Vol. 9, Issue 8
DOI: 10.1039/c0pp00019a

Inhibition of HSV-1 protease by benzoxazinones
journal, October 1996

Jarvest, Richard L.; Parratt, Martin J.; Debouck, Christine M.
Bioorganic & Medicinal Chemistry Letters, Vol. 6, Issue 20
DOI: 10.1016/0960-894X(96)00455-6

2-Substituted benzoxazinone analogues as anti-human coronavirus (anti-HCoV) and ICAM-1 expression inhibition agents
journal, September 2004

Hsieh, Pei-Wen; Chang, Fang-Rong; Chang, Cheng-Hsien
Bioorganic & Medicinal Chemistry Letters, Vol. 14, Issue 18
DOI: 10.1016/j.bmcl.2004.06.083

Role of Ground State Structure in Photoinduced Tautomerization in Bifunctional Proton Donor−Acceptor Molecules: 1H-Pyrrolo[3,2- h ]quinoline and Related Compounds
journal, December 1999

Kyrychenko, A.; Herbich, J.; Izydorzak, M.
Journal of the American Chemical Society, Vol. 121, Issue 48
DOI: 10.1021/ja991817z

Oxidation of Indole by Cytochrome P450 Enzymes ^†
journal, November 2000

Gillam, Elizabeth M. J.; Notley, Lisa M.; Cai, Hongliang
Biochemistry, Vol. 39, Issue 45
DOI: 10.1021/bi001229u

Photodynamically Generated Bovine Serum Albumin Radicals: Evidence for Damage Transfer and Oxidation at Cysteine and Tryptophan Residues
journal, March 1998

Silvester, Julie A.; Timmins, Graham S.; Davies, Michael J.
Free Radical Biology and Medicine, Vol. 24, Issue 5
DOI: 10.1016/S0891-5849(97)00327-4

Design and synthesis of 4H-3,1-benzoxazin-4-ones as potent alternate substrate inhibitors of human leukocyte elastase
journal, February 1990

Krantz, Allen; Spencer, Robin W.; Tam, Tim F.
Journal of Medicinal Chemistry, Vol. 33, Issue 2
DOI: 10.1021/jm00164a002

Similar Records in DOE PAGES and OSTI.GOV collections:

Photoinduced oxidation of an indole derivative: 2-(1' H -indol-2'-yl)-[1,5]naphthyridine

Journal Article Golec, Barbara ; Nawara, Krzysztof ; Thummel, Randolph P. ; ... - Photochemical & Photobiological Sciences

UV-induced photooxidation of a 2-substituted indole derivative provides an efficient way for the formation of a benzoxazinone derivative.
https://doi.org/10.1039/c8pp00587g
Structure-Based Discovery of 4-(6-Methoxy-2-methyl-4-(quinolin-4-yl)-9 H -pyrimido[4,5- b ]indol-7-yl)-3,5-dimethylisoxazole (CD161) as a Potent and Orally Bioavailable BET Bromodomain Inhibitor

Journal Article Zhao, Yujun ; Bai, Longchuan ; Liu, Liu ; ... - Journal of Medicinal Chemistry

We have designed and synthesized 9H-pyrimido[4,5-b]indole-containing compounds to obtain potent and orally bioavailable BET inhibitors. By incorporation of an indole or a quinoline moiety to the 9H-pyrimido[4,5-b]indole core, we identified a series of small molecules showing high binding affinities to BET proteins and low nanomolar potencies in inhibition of cell growth in acute leukemia cell lines. One such compound, 4-(6-methoxy-2-methyl-4-(quinolin-4-yl)-9H-pyrimido[4,5-b]indol-7-yl)-3,5-dimethylisoxazole (31) has excellent microsomal stability and good oral pharmacokinetics in rats and mice. Orally administered, 31 achieves significant antitumor activity in the MV4;11 leukemia and MDA-MB-231 triple-negative breast cancer xenograft models in mice. Determination of the cocrystal structure of 31more »« less
Cited by 16
https://doi.org/10.1021/acs.jmedchem.7b00193

Full Text Available
Radioprotection (uv and gamma rays) of DNA molecule by indole and indole- derivatives

Journal Article Tomicic, I ; Pieber, M ; Romero, C ; ... - Z. Naturforsch., c, v. 28c, no. 7/8, pp. 379-385

The radioprotective ability of L-tryptophan, tryptamine, 3indoleacetic acid, and indole (10/sup -4/ M), on uv- and gamma-irradiated DNA (10/sup -4/ M) is studied. UV radioprotection is accomplished in the following order of efficiency: L-tryptophan and 3-indoleacetic acid> indole and tryptamine. The corresponding DRF (dose reduction factor) measured as absorbancy loss at 260 nm, were: L-tryptophan and 3-indoleacetic acid around 3 and tryptamine and indole around 1. When absorbancy loss plus changes in the patterns of the absorbancy curve were considered the DRF was: Ltryptophan 2.53, 3-indoleacetic acid 1.54, indole 1.22, and tryptamine 0.75, respectively. For gamma radiation damage the ordermore »« less
Thermodynamics and the hydrodenitrogenation of indole: Part 1, Thermodynamic properties of indoline and 2-methylindole: Part 2, Gibbs energies of reaction in the hydrodenitrogenation of indole: Part 3, Thermodynamic equilibria and comparison with literature kinetic

Technical Report Steele, W. V. ; Chirico, R. D.

Ideal-gas thermodynamic properties for indoline and 2-methylindole based on accurate calorimetric measurements (between 300 to 500 K and 300 to 700 K, respectively) were determined; well into the range of typical chemical process temperatures. The calorimetrically derived values provide a firm basis for the prediction of thermodynamic properties for a large family of structures including many substituted indoles and indolines. Critical-temperature/density measurements obtained using a differential scanning calorimeter (DSC) are reported for 2-methylindole. A critical pressure and acentric factor are derived for 2-methylindole. Group-additivity estimation methods are employed to estimate the Gibbs energies of formation for the reactants, intermediates, andmore »« less
https://doi.org/10.2172/6124014

Full Text Available
Acyl Glucuronide Metabolites of 6-Chloro-5-[4-(1-hydroxycyclobutyl)phenyl]-1H-indole-3-carboxylic Acid (PF-06409577) and Related Indole-3-carboxylic Acid Derivatives are Direct Activators of Adenosine Monophosphate-Activated Protein Kinase (AMPK)

Journal Article Ryder, Tim F. ; Calabrese, Matthew F. ; Walker, Gregory S. ; ... - Journal of Medicinal Chemistry

Studies on indole-3-carboxylic acid derivatives as direct activators of human adenosine monophosphate-activated protein kinase (AMPK) α1β1γ1 isoform have culminated in the identification of PF-06409577 (1), PF-06885249 (2), and PF-06679142 (3) as potential clinical candidates. Compounds 1–3 are primarily cleared in animals and humans via glucuronidation. In this paper, we describe the biosynthetic preparation, purification, and structural characterization of the glucuronide conjugates of 1–3. Spectral characterization of the purified glucuronides M1, M2, and M3 indicated that they were acyl glucuronide derivatives. In vitro pharmacological evaluation revealed that all three acyl glucuronides retained selective activation of β1-containing AMPK isoforms. Inhibition of demore »« less
Cited by 3
https://doi.org/10.1021/acs.jmedchem.8b00807

Full Text Available

Similar Records

Title: Photoinduced oxidation of an indole derivative: 2-(1′ H -indol-2′-yl)-[1,5]naphthyridine

Abstract

Citation Formats

Oxidation of 2-arylindoles for synthesis of 2-arylbenzoxazinones with oxone as the sole oxidant journal, January 2013

1,4-Benzothiazine and 1,4-Benzoxazine imidazole derivatives with antifungal activity: A docking study journal, November 2002

Light emission from tryptophan oxidation by hypobromous acid: Light emission from tryptophan oxidation by hypobromous acid journal, October 2012

Studies on Some Benzoxazine-4-one Derivatives with Potential Biological Activity journal, May 2012

Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density journal, January 1988

Copper-mediated oxidative tandem reactions with molecular oxygen: synthesis of 2-arylbenzoxazinone derivatives from indoles journal, April 2014

Synthesis of Isatins by I 2 /TBHP Mediated Oxidation of Indoles journal, May 2014

Density-functional exchange-energy approximation with correct asymptotic behavior journal, September 1988

Protect from Light: Photodegradation and Protein Biologics journal, June 2007

Dissociative Excitation Energy Transfer in the Reactions of Protonated Cysteine and Tryptophan with Electronically Excited Singlet Molecular Oxygen (a 1 Δ g ) journal, August 2011

Synthesis of 2-Oxindoles from Substituted Indoles by Hypervalent-Iodine Oxidation: Synthesis of 2-Oxindoles from Substituted Indoles by Hypervalent-Iodine Oxidation journal, March 2018

Structure and Photophysics of 2-(2‘-Pyridyl)benzindoles: The Role of Intermolecular Hydrogen Bonds journal, November 2007

The Photophysics and Photochemistry of the Near-Uv Absorbing Amino Acids-I. Tryptophan and its Simple Derivatives journal, April 1984

Altering the regioselectivity of cytochrome P450 BM-3 by saturation mutagenesis for the biosynthesis of indirubin journal, November 2010

Light-Induced Oxidation of Tryptophan and Histidine. Reactivity of Aromatic N -Heterocycles toward Triplet-Excited Flavins journal, June 2009

Temperature dependent steric hindrance effects in triplet state relaxation of meso-phenyl-substituted Pd-octaethylporphyrins journal, March 2018

Expansion of Substrate Specificity of Cytochrome P450 2A6 by Random and Site-directed Mutagenesis journal, October 2005

Tryptophan oxidation photosensitized by pterin journal, October 2013

The photochemistry of indomethacin journal, September 1991

Synthesis and evaluation of condensed and noncondensed heterocyclic compounds of industrial application journal, September 2006

Inhibition of human chymase by 2-amino-3,1-benzoxazin-4-ones journal, April 2001

Photooxidation of Tryptophan and Tyrosine Residues in Human Serum Albumin Sensitized by Pterin: A Model for Globular Protein Photodamage in Skin journal, August 2016

Solvent-Induced Changes in Photophysics and Photostability of Indole-Naphthyridines journal, December 2014

Irreversible Inhibitors of Serine, Cysteine, and Threonine Proteases journal, December 2002

Rotational isomerism in trans-1,2-diarylethylenes journal, December 1991

Optimization of bio-indigo production by recombinant E. coli harboring fmo gene journal, June 2008

Synthesis and evaluation of benzoxazinone derivatives on activity of human neutrophil elastase and on hemorrhagic shock-induced lung injury in rats journal, July 2010

Solvent-Induced s yn − a nti Rotamerization of 2-(2‘-Pyridyl)indole and the Structure of its Alcohol Complexes journal, March 2000

Expression of naphthalene oxidation genes in Escherichia coli results in the biosynthesis of indigo journal, October 1983

New method for the synthesis of 3(2H)-pyridazinones and their alkene precursors: Solvent-free reactions under microwave irradiation journal, September 1995

Mechanism for slow-binding inhibition of human leukocyte elastase by valine-derived benzoxazinones journal, June 1987

The Witkop-Winterfeldt-Oxidation of Indoles journal, January 2007

Geometric isomerism in the phenylhydrazones of some .alpha.-dicarbonyl compounds journal, March 1978

Photooxygenation of Heterocycles journal, January 2005

Construction of Metabolic Operons Catalyzing the De Novo Biosynthesis of Indigo in Escherichia coli journal, March 1993

Photooxidation of Tryptophan Leading to 2-Aminoacetophenone - A Possible Reason for the Untypical Aging Off-flavor in Wine journal, August 2014

Combined effect of hydrogen bonding interactions and freezing of rotameric equilibrium on the enhancement of photostability journal, January 2018

Phenyl-substituted porphyrins. 1. Synthesis of meso-phenyl-substituted porphyrins journal, October 2004

Investigation on the phototransformation of tadalafil in aqueous media. 6-Epimerization vs. solvent trapping reaction journal, January 2010

Inhibition of HSV-1 protease by benzoxazinones journal, October 1996

2-Substituted benzoxazinone analogues as anti-human coronavirus (anti-HCoV) and ICAM-1 expression inhibition agents journal, September 2004

Role of Ground State Structure in Photoinduced Tautomerization in Bifunctional Proton Donor−Acceptor Molecules: 1H-Pyrrolo[3,2- h ]quinoline and Related Compounds journal, December 1999

Oxidation of Indole by Cytochrome P450 Enzymes † journal, November 2000

Photodynamically Generated Bovine Serum Albumin Radicals: Evidence for Damage Transfer and Oxidation at Cysteine and Tryptophan Residues journal, March 1998

Design and synthesis of 4H-3,1-benzoxazin-4-ones as potent alternate substrate inhibitors of human leukocyte elastase journal, February 1990

Oxidation of 2-arylindoles for synthesis of 2-arylbenzoxazinones with oxone as the sole oxidant
journal, January 2013

1,4-Benzothiazine and 1,4-Benzoxazine imidazole derivatives with antifungal activity: A docking study
journal, November 2002

Light emission from tryptophan oxidation by hypobromous acid: Light emission from tryptophan oxidation by hypobromous acid
journal, October 2012

Studies on Some Benzoxazine-4-one Derivatives with Potential Biological Activity
journal, May 2012

Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density
journal, January 1988

Copper-mediated oxidative tandem reactions with molecular oxygen: synthesis of 2-arylbenzoxazinone derivatives from indoles
journal, April 2014

Synthesis of Isatins by I ₂ /TBHP Mediated Oxidation of Indoles
journal, May 2014

Density-functional exchange-energy approximation with correct asymptotic behavior
journal, September 1988

Protect from Light: Photodegradation and Protein Biologics
journal, June 2007

Dissociative Excitation Energy Transfer in the Reactions of Protonated Cysteine and Tryptophan with Electronically Excited Singlet Molecular Oxygen (a ¹ Δ _g )
journal, August 2011

Synthesis of 2-Oxindoles from Substituted Indoles by Hypervalent-Iodine Oxidation: Synthesis of 2-Oxindoles from Substituted Indoles by Hypervalent-Iodine Oxidation
journal, March 2018

Structure and Photophysics of 2-(2‘-Pyridyl)benzindoles: The Role of Intermolecular Hydrogen Bonds
journal, November 2007

The Photophysics and Photochemistry of the Near-Uv Absorbing Amino Acids-I. Tryptophan and its Simple Derivatives
journal, April 1984

Altering the regioselectivity of cytochrome P450 BM-3 by saturation mutagenesis for the biosynthesis of indirubin
journal, November 2010

Light-Induced Oxidation of Tryptophan and Histidine. Reactivity of Aromatic N -Heterocycles toward Triplet-Excited Flavins
journal, June 2009

Temperature dependent steric hindrance effects in triplet state relaxation of meso-phenyl-substituted Pd-octaethylporphyrins
journal, March 2018

Expansion of Substrate Specificity of Cytochrome P450 2A6 by Random and Site-directed Mutagenesis
journal, October 2005

Tryptophan oxidation photosensitized by pterin
journal, October 2013

The photochemistry of indomethacin
journal, September 1991

Synthesis and evaluation of condensed and noncondensed heterocyclic compounds of industrial application
journal, September 2006

Inhibition of human chymase by 2-amino-3,1-benzoxazin-4-ones
journal, April 2001

Photooxidation of Tryptophan and Tyrosine Residues in Human Serum Albumin Sensitized by Pterin: A Model for Globular Protein Photodamage in Skin
journal, August 2016

Solvent-Induced Changes in Photophysics and Photostability of Indole-Naphthyridines
journal, December 2014

Irreversible Inhibitors of Serine, Cysteine, and Threonine Proteases
journal, December 2002

Rotational isomerism in trans-1,2-diarylethylenes
journal, December 1991

Optimization of bio-indigo production by recombinant E. coli harboring fmo gene
journal, June 2008

Synthesis and evaluation of benzoxazinone derivatives on activity of human neutrophil elastase and on hemorrhagic shock-induced lung injury in rats
journal, July 2010

Solvent-Induced s yn − a nti Rotamerization of 2-(2‘-Pyridyl)indole and the Structure of its Alcohol Complexes
journal, March 2000

Expression of naphthalene oxidation genes in Escherichia coli results in the biosynthesis of indigo
journal, October 1983

New method for the synthesis of 3(2H)-pyridazinones and their alkene precursors: Solvent-free reactions under microwave irradiation
journal, September 1995

Mechanism for slow-binding inhibition of human leukocyte elastase by valine-derived benzoxazinones
journal, June 1987

The Witkop-Winterfeldt-Oxidation of Indoles
journal, January 2007

Geometric isomerism in the phenylhydrazones of some .alpha.-dicarbonyl compounds
journal, March 1978

Photooxygenation of Heterocycles
journal, January 2005

Construction of Metabolic Operons Catalyzing the De Novo Biosynthesis of Indigo in Escherichia coli
journal, March 1993

Photooxidation of Tryptophan Leading to 2-Aminoacetophenone - A Possible Reason for the Untypical Aging Off-flavor in Wine
journal, August 2014

Combined effect of hydrogen bonding interactions and freezing of rotameric equilibrium on the enhancement of photostability
journal, January 2018

Phenyl-substituted porphyrins. 1. Synthesis of meso-phenyl-substituted porphyrins
journal, October 2004

Investigation on the phototransformation of tadalafil in aqueous media. 6-Epimerization vs. solvent trapping reaction
journal, January 2010

Inhibition of HSV-1 protease by benzoxazinones
journal, October 1996

2-Substituted benzoxazinone analogues as anti-human coronavirus (anti-HCoV) and ICAM-1 expression inhibition agents
journal, September 2004

Role of Ground State Structure in Photoinduced Tautomerization in Bifunctional Proton Donor−Acceptor Molecules: 1H-Pyrrolo[3,2- h ]quinoline and Related Compounds
journal, December 1999

Oxidation of Indole by Cytochrome P450 Enzymes ^†
journal, November 2000

Photodynamically Generated Bovine Serum Albumin Radicals: Evidence for Damage Transfer and Oxidation at Cysteine and Tryptophan Residues
journal, March 1998

Design and synthesis of 4H-3,1-benzoxazin-4-ones as potent alternate substrate inhibitors of human leukocyte elastase
journal, February 1990