Development and Binding Mode Assessment of N-[4-[2-Propyn-1-yl[(6S)-4,6,7,8-tetrahydro-2-(hydroxymethyl)-4-oxo-3H-cyclopenta[g]quinazolin-6-yl]amino]benzoyl]-l-γ-glutamyl-d-glutamic Acid (BGC 945), a Novel Thymidylate Synthase Inhibitor That Targets Tumor Cells

Anna Tochowicz; Sean Dalziel; Oliv Eidam; Joseph D. O’Connell; Sarah Griner; Janet S. Finer-Moore; Robert M. Stroud

doi:10.1021/jm400490e

Development and Binding Mode Assessment of N-[4-[2-Propyn-1-yl[(6S)-4,6,7,8-tetrahydro-2-(hydroxymethyl)-4-oxo-3H-cyclopenta[g]quinazolin-6-yl]amino]benzoyl]-l-γ-glutamyl-d-glutamic Acid (BGC 945), a Novel Thymidylate Synthase Inhibitor That Targets Tumor Cells

Journal of Medicinal Chemistry ◽

10.1021/jm400490e ◽

2013 ◽

Vol 56 (13) ◽

pp. 5446-5455 ◽

Cited By ~ 10

Author(s):

Anna Tochowicz ◽

Sean Dalziel ◽

Oliv Eidam ◽

Joseph D. O’Connell ◽

Sarah Griner ◽

...

Keyword(s):

Glutamic Acid ◽

Tumor Cells ◽

Thymidylate Synthase ◽

Binding Mode ◽

Thymidylate Synthase Inhibitor ◽

Synthase Inhibitor

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ChemInform Abstract: Syntheses of a Regioisomer of N-(4-(2-(2-Amino-4(3H)-oxo-7H-pyrrolo(2, 3-d)pyrimidin-5-yl)ethyl)benzoyl)-L -glutamic Acid (LY231514), an Active Thymidylate Synthase Inhibitor and Antitumor Agent.

ChemInform ◽

10.1002/chin.199403177 ◽

2010 ◽

Vol 25 (3) ◽

pp. no-no

Author(s):

E. C. TAYLOR ◽

W. B. YOUNG ◽

R. CHAUDHARI ◽

H. H. PATEL

Keyword(s):

Glutamic Acid ◽

Thymidylate Synthase ◽

Antitumor Agent ◽

Thymidylate Synthase Inhibitor ◽

Synthase Inhibitor

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ChemInform Abstract: Chemoenzymatic Preparation of the Novel Antifolate Thymidylate Synthase Inhibitor N-(4-{N-[(6S)-2-Methyl-4-oxo-3,4,7,8-tetrahydro-6H-cyclopenta [g]quinazolin-6-yl]-N-(prop-2-ynyl)amino}benzoyl)-L-glutamic Acid (Ia) and Its Glutamyl Cl

ChemInform ◽

10.1002/chin.199937221 ◽

2010 ◽

Vol 30 (37) ◽

pp. no-no

Author(s):

Jonathan H. Marriott ◽

Stephen Neidle ◽

Zbigniew Matusiak ◽

Vassilios Bavetsias ◽

Ann L. Jackman ◽

...

Keyword(s):

Glutamic Acid ◽

Thymidylate Synthase ◽

The Novel ◽

Thymidylate Synthase Inhibitor ◽

Synthase Inhibitor

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Syntheses of a Regioisomer of N-{4-[2-(2-Amino-4(3H)-oxo-7H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl}-L-glutamic Acid (LY231514), an Active Thymidylate Synthase Inhibitor and Antitumor Agent

Heterocycles ◽

10.3987/com-93-6400 ◽

1993 ◽

Vol 36 (8) ◽

pp. 1897 ◽

Cited By ~ 8

Author(s):

Edward C. Taylor ◽

Wendy B. Young ◽

Rajendra Chaudhari ◽

Hemantkumar H. Patel

Keyword(s):

Glutamic Acid ◽

Thymidylate Synthase ◽

Antitumor Agent ◽

Thymidylate Synthase Inhibitor ◽

Synthase Inhibitor

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Chemoenzymatic preparation of the novel antifolate thymidylate synthase inhibitor N-(4-{N-[(6S )-2-methyl-4-oxo-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl]-N-(prop-2-ynyl)amino}benzoyl)-L-glutamic acid and its glutamyl cleavage product

Journal of the Chemical Society Perkin Transactions 1 ◽

10.1039/a901141b ◽

1999 ◽

pp. 1495-1504 ◽

Cited By ~ 8

Author(s):

Jonathan H. Marriott ◽

Stephen Neidle ◽

Zbigniew Matusiak ◽

Vassilios Bavetsias ◽

Ann L. Jackman ◽

...

Keyword(s):

Glutamic Acid ◽

Thymidylate Synthase ◽

Cleavage Product ◽

The Novel ◽

Thymidylate Synthase Inhibitor ◽

Synthase Inhibitor

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Mechanisms of resistance to N-[5-[N-(3, 4-dihydro-2-methyl-4-oxoquinazolin-6-ylmethyl)-N-methylamino]-2-thenoyl]-L-glutamic acid (ZD1694), a folate-based thymidylate synthase inhibitor, in the HCT-8 human ileocecal adenocarcinoma cell line

Biochemical Pharmacology ◽

10.1016/0006-2952(95)00135-m ◽

1995 ◽

Vol 50 (3) ◽

pp. 391-398 ◽

Cited By ~ 25

Author(s):

Kun Lu ◽

Ming-Biao Yin ◽

John J. McGuire ◽

Enzo Bonmassar ◽

Youcef M. Rustum

Keyword(s):

Glutamic Acid ◽

Cell Line ◽

Thymidylate Synthase ◽

Mechanisms Of Resistance ◽

Adenocarcinoma Cell Line ◽

Adenocarcinoma Cell ◽

Thymidylate Synthase Inhibitor ◽

Synthase Inhibitor

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Phase I, Pharmacokinetic and Biological Correlative Study of OSI-7904L, a Novel Liposomal Thymidylate Synthase Inhibitor, and Cisplatin in Patients with Solid Tumors

Clinical Cancer Research ◽

10.1158/1078-0432.ccr-08-0864 ◽

2008 ◽

Vol 14 (23) ◽

pp. 7947-7955 ◽

Cited By ~ 9

Author(s):

Alejandro D. Ricart ◽

Jordan D. Berlin ◽

Kyriakos P. Papadopoulos ◽

Samira Syed ◽

Daniel W. Drolet ◽

...

Keyword(s):

Phase I ◽

Solid Tumors ◽

Thymidylate Synthase ◽

Correlative Study ◽

Thymidylate Synthase Inhibitor ◽

Synthase Inhibitor

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The Antitumour Activity of ZD9331, a Non-Polyglutamatable Quinazoline Thymidylate Synthase Inhibitor

Purine and Pyrimidine Metabolism in Man VIII - Advances in Experimental Medicine and Biology ◽

10.1007/978-1-4615-2584-4_40 ◽

1995 ◽

pp. 185-188 ◽

Cited By ~ 14

Author(s):

Ann L. Jackman ◽

Rosemary Kimbell ◽

Melody Brown ◽

Lisa Brunton ◽

Kenneth R. Harrap ◽

...

Keyword(s):

Thymidylate Synthase ◽

Antitumour Activity ◽

Thymidylate Synthase Inhibitor ◽

Synthase Inhibitor

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Polyglutamation of the Thymidylate Synthase Inhibitor, N10-Propargyl-5,8-Dideazafolic Acid (CB 3717), in Organs of Ehrlich Ascites Carcinoma-Bearing Mice

Montreal, Canada, June 15–20, 1986 ◽

10.1515/9783110856262-190 ◽

1986 ◽

pp. 993-996

Keyword(s):

Thymidylate Synthase ◽

Ehrlich Ascites Carcinoma ◽

Ehrlich Ascites ◽

Thymidylate Synthase Inhibitor ◽

Synthase Inhibitor

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A phase I study of the lipophilic thymidylate synthase inhibitor Thymitaq™ (nolatrexed dihydrochloride) given by 10-day oral administration

British Journal of Cancer ◽

10.1038/sj.bjc.6690146 ◽

1999 ◽

Vol 79 (5-6) ◽

pp. 915-920 ◽

Cited By ~ 9

Author(s):

D I Jodrell ◽

A Bowman ◽

R Rye ◽

B Byrne ◽

A Boddy ◽

...

Keyword(s):

Oral Administration ◽

Phase I ◽

Thymidylate Synthase ◽

Phase I Study ◽

Thymidylate Synthase Inhibitor ◽

Synthase Inhibitor

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New Synthesis of Thymidylate Synthase Inhibitor Raltitrexed

Synthetic Communications ◽

10.1081/scc-120024732 ◽

2003 ◽

Vol 33 (20) ◽

pp. 3519-3526 ◽

Cited By ~ 6

Author(s):

Sheng-Li Cao ◽

Rong Wan ◽

Yu-Ping Feng

Keyword(s):

Thymidylate Synthase ◽

New Synthesis ◽

Thymidylate Synthase Inhibitor ◽

Synthase Inhibitor

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