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Synthesis of novel, nonclassical 2-amino-4-oxo-6-(arylthio)ethylpyrrolo[2,3-d] pyrimidines as potential inhibitors of thymidylate synthase

✍ Scribed by Aleem Gangjee; Nauzer P. Dubash; Roy L. Kisliuk

Publisher
Journal of Heterocyclic Chemistry
Year
2001
Tongue
English
Weight
66 KB
Volume
38
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

A novel series of 14 nonclassical 6‐substituted pyrrolo[2,3‐d]pyrimidines 2a ‐ 2n were designed as potential inhibitors of thymidylate synthase, based on previously reported 2‐amino‐4‐oxopyrrolo[2,3‐d]‐pyrimidines 1a and 1b. The synthesis of the target compounds 2a‐2n was accomplished by nucleophilic displacement of the mesylate 11 with appropriately substituted aromatic thiols. Most of the target compounds did not show inhibition of either Escherichia coli thymidylate synthase or recombinant human thymidylate synthase at the concentrations tested. However, compounds 2h (2,4‐dichloro), 2j (3,4‐dichloro) and 2m (4‐nitro) did show 25%, 40% and 35% inhibition of human thymidylate synthase at 23 μM, 23 μM and 24 μM, respectively. These observations are in accordance with previous reports, which suggest that strong electron withdrawing substituents on the side chain aromatic ring are conducive to inhibition of thymidylate synthase.

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ChemInform Abstract: Synthesis of Novel,
ChemInform Abstract: Synthesis of Novel, Nonclassical 2-Amino-4-oxo-6-(arylthio)ethylpyrrolo[2,3-d]pyrimidines as Potential Inhibitors of Thymidylate Synthase.
✍ Aleem Gangjee; Nauzer P. Dubash; Roy L. Kisliuk 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 30 KB 👁 1 views

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Synthesis of classical and nonclassical
Synthesis of classical and nonclassical 2-amino-4-oxo-6-benzylthieno-[2,3-d]pyrimidines as potential thymidylate synthase inhibitors
✍ Aleem Gangjee; Yibin Qiu; Roy L. Kisliuk 📂 Article 📅 2004 🏛 Journal of Heterocyclic Chemistry 🌐 English ⚖ 97 KB

## Abstract A series of seven nonclassical 2‐amino‐4‐oxo‐6‐substituted thieno[2,3‐__d__]pyrimidines **2‐8** and one classical __N__‐[4‐(2‐amino‐4‐oxo‐3,4‐dihydrothieno[2,3‐__d__]pyrimidin‐6‐ylmethyl)benzoyl]‐L‐glutamic acid **9** (Table I) were designed as the first in a series of 6‐substituted 6‐5