Literature DB >> 1447744

A dideazatetrahydrofolate analogue lacking a chiral center at C-6, N-[4-[2-(2-amino-3,4-dihydro-4-oxo-7H-pyrrolo[2,3-d]pyrimidin-5- yl)ethyl]benzoyl]-L-glutamic acid, is an inhibitor of thymidylate synthase.

E C Taylor1, D Kuhnt, C Shih, S M Rinzel, G B Grindey, J Barredo, M Jannatipour, R G Moran.   

Abstract

N-[4-[2-(2-Amino-3,4-dihydro-4-oxo-7H-pyrrolo[2,3-d]pyrimidin-5- yl)ethyl]benzoyl]-L-glutamic acid (15), prepared in five steps from 2-pivaloyl-7-deazaguanine, has been found to be an antitumor agent with its primary site of action at thymidylate synthase rather than purine synthesis. This compound appears to be a promising candidate for clinical evaluation.

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Year:  1992        PMID： 1447744     DOI： 10.1021/jm00101a023

Source DB:  PubMed          Journal:  J Med Chem        ISSN： 0022-2623            Impact factor:   7.446


  43 in total

1.  High expression of folate receptor alpha in lung cancer correlates with adenocarcinoma histology and EGFR [corrected] mutation.

Authors:  Maria Ines Nunez; Carmen Behrens; Denise M Woods; Heather Lin; Milind Suraokar; Humam Kadara; Wayne Hofstetter; Neda Kalhor; J Jack Lee; Wilbur Franklin; David J Stewart; Ignacio I Wistuba
Journal:  J Thorac Oncol       Date:  2012-05       Impact factor: 15.609

2.  The membrane transport and polyglutamation of pralatrexate: a new-generation dihydrofolate reductase inhibitor.

Authors:  Michele Visentin; Ersin Selcuk Unal; Rongbao Zhao; I David Goldman
Journal:  Cancer Chemother Pharmacol       Date:  2013-07-24       Impact factor: 3.333

3.  Potent dual thymidylate synthase and dihydrofolate reductase inhibitors: classical and nonclassical 2-amino-4-oxo-5-arylthio-substituted-6-methylthieno[2,3-d]pyrimidine antifolates.

Authors:  Aleem Gangjee; Yibin Qiu; Wei Li; Roy L Kisliuk
Journal:  J Med Chem       Date:  2008-09-25       Impact factor: 7.446

4.  Fragment-based discovery of novel thymidylate synthase leads by NMR screening and group epitope mapping.

Authors:  Darren W Begley; Suxin Zheng; Gabriele Varani
Journal:  Chem Biol Drug Des       Date:  2010-07-05       Impact factor: 2.817

Review 5.  Phenotypic screening in cancer drug discovery - past, present and future.

Authors:  John G Moffat; Joachim Rudolph; David Bailey
Journal:  Nat Rev Drug Discov       Date:  2014-07-18       Impact factor: 84.694

6.  Synthesis of classical, four-carbon bridged 5-substituted furo[2,3-d]pyrimidine and 6-substituted pyrrolo[2,3-d]pyrimidine analogues as antifolates.

Authors:  Aleem Gangjee; Yibin Zeng; John J McGuire; Roy L Kisliuk
Journal:  J Med Chem       Date:  2005-08-11       Impact factor: 7.446

7.  2,4-Diamino-5-methyl-6-substituted arylthio-furo[2,3-d]pyrimidines as novel classical and nonclassical antifolates as potential dual thymidylate synthase and dihydrofolate reductase inhibitors.

Authors:  Aleem Gangjee; Hiteshkumar D Jain; Jaclyn Phan; Xin Guo; Sherry F Queener; Roy L Kisliuk
Journal:  Bioorg Med Chem       Date:  2009-12-26       Impact factor: 3.641

8.  Lymph node dissection in primary intrahepatic malignant mesothelioma: case report and implications for diagnosis and therapy.

Authors:  Bettina M Buchholz; Ines Gütgemann; Hans-Peter Fischer; Marcus Gorschlüter; Andreas Türler; Jörg C Kalff; Andreas Hirner; Jens Standop
Journal:  Langenbecks Arch Surg       Date:  2009-03-12       Impact factor: 3.445

9.  Design, synthesis, and X-ray crystal structure of classical and nonclassical 2-amino-4-oxo-5-substituted-6-ethylthieno[2,3-d]pyrimidines as dual thymidylate synthase and dihydrofolate reductase inhibitors and as potential antitumor agents.

Authors:  Aleem Gangjee; Wei Li; Roy L Kisliuk; Vivian Cody; Jim Pace; Jennifer Piraino; Jennifer Makin
Journal:  J Med Chem       Date:  2009-08-13       Impact factor: 7.446

10.  Phase II trial of S-1 and cisplatin with concurrent radiotherapy for locally advanced non-small-cell lung cancer.

Authors:  F Ohyanagi; N Yamamoto; A Horiike; H Harada; T Kozuka; H Murakami; K Gomi; T Takahashi; M Morota; T Nishimura; M Endo; Y Nakamura; A Tsuya; T Horai; M Nishio
Journal:  Br J Cancer       Date:  2009-07-21       Impact factor: 7.640
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