Literature DB >> 8958183

A simplified and efficient synthesis of 5,10-dideaza-5,6,7,8-tetrahydrofolic acid (DDATHF).

E C Taylor1, R Chaudhari, K Lee.   

Abstract

A new and extremely efficient synthesis of DDATHF from 4-vinylbenzoic acid and bromomalondialdehyde as precursors has been developed which proceeds in 48% overall yield.

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Year:  1996        PMID: 8958183     DOI: 10.1007/bf00194531

Source DB:  PubMed          Journal:  Invest New Drugs        ISSN: 0167-6997            Impact factor:   3.850


  11 in total

1.  A new folate antimetabolite, 5,10-dideaza-5,6,7,8-tetrahydrofolate is a potent inhibitor of de novo purine synthesis.

Authors:  G P Beardsley; B A Moroson; E C Taylor; R G Moran
Journal:  J Biol Chem       Date:  1989-01-05       Impact factor: 5.157

Review 2.  Design and synthesis of inhibitors of folate-dependent enzymes as antitumor agents.

Authors:  E C Taylor
Journal:  Adv Exp Med Biol       Date:  1993       Impact factor: 2.622

3.  Synthesis of the antileukemic agents 5,10-dideazaaminopterin and 5,10-dideaza-5,6,7,8-tetrahydroaminopterin.

Authors:  E C Taylor; P J Harrington; S R Fletcher; G P Beardsley; R G Moran
Journal:  J Med Chem       Date:  1985-07       Impact factor: 7.446

4.  Intracellular metabolism of 5,10-dideazatetrahydrofolic acid in human leukemia cell lines.

Authors:  G Pizzorno; J A Sokoloski; A R Cashmore; B A Moroson; A D Cross; G P Beardsley
Journal:  Mol Pharmacol       Date:  1991-01       Impact factor: 4.436

5.  Synthesis and antifolate activity of 5-methyl-5,10-dideaza analogues of aminopterin and folic acid and an alternative synthesis of 5,10-dideazatetrahydrofolic acid, a potent inhibitor of glycinamide ribonucleotide formyltransferase.

Authors:  J R Piper; G S McCaleb; J A Montgomery; R L Kisliuk; Y Gaumont; J Thorndike; F M Sirotnak
Journal:  J Med Chem       Date:  1988-11       Impact factor: 7.446

6.  Synthesis and biological properties of 5,10-dideaza-5,6,7,8-tetrahydrofolic acid.

Authors:  D H Boschelli; S Webber; J M Whiteley; A L Oronsky; S S Kerwar
Journal:  Arch Biochem Biophys       Date:  1988-08-15       Impact factor: 4.013

7.  Multifactorial resistance to 5,10-dideazatetrahydrofolic acid in cell lines derived from human lymphoblastic leukemia CCRF-CEM.

Authors:  G Pizzorno; B A Moroson; A R Cashmore; O Russello; J R Mayer; J Galivan; M A Bunni; D G Priest; G P Beardsley
Journal:  Cancer Res       Date:  1995-02-01       Impact factor: 12.701

8.  Substrate specificity of mammalian folylpolyglutamate synthetase for 5,10-dideazatetrahydrofolate analogs.

Authors:  L L Habeck; L G Mendelsohn; C Shih; E C Taylor; P D Colman; L S Gossett; T A Leitner; R M Schultz; S L Andis; R G Moran
Journal:  Mol Pharmacol       Date:  1995-08       Impact factor: 4.436

9.  Carrier- and receptor-mediated transport of folate antagonists targeting folate-dependent enzymes: correlates of molecular-structure and biological activity.

Authors:  G R Westerhof; J H Schornagel; I Kathmann; A L Jackman; A Rosowsky; R A Forsch; J B Hynes; F T Boyle; G J Peters; H M Pinedo
Journal:  Mol Pharmacol       Date:  1995-09       Impact factor: 4.436

10.  Structural features of 5,10-dideaza-5,6,7,8-tetrahydrofolate that determine inhibition of mammalian glycinamide ribonucleotide formyltransferase.

Authors:  S W Baldwin; A Tse; L S Gossett; E C Taylor; A Rosowsky; C Shih; R G Moran
Journal:  Biochemistry       Date:  1991-02-19       Impact factor: 3.162

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  2 in total

1.  Synthesis of (6R)- and (6S)-5,10-dideazatetrahydrofolate oligo-gamma-glutamates: kinetics of multiple glutamate ligations catalyzed by folylpoly-gamma-glutamate synthetase.

Authors:  John W Tomsho; John J McGuire; James K Coward
Journal:  Org Biomol Chem       Date:  2005-08-15       Impact factor: 3.876

Review 2.  Folic Acid Antimetabolites (Antifolates): A Brief Review on Synthetic Strategies and Application Opportunities.

Authors:  Igor S Kovalev; Grigory V Zyryanov; Sougata Santra; Adinath Majee; Mikhail V Varaksin; Valery N Charushin
Journal:  Molecules       Date:  2022-09-22       Impact factor: 4.927

  2 in total

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