Literature DB >> 4009615

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

E C Taylor, P J Harrington, S R Fletcher, G P Beardsley, R G Moran.   

Abstract

Total syntheses from pyridine precursors of 5,10-dideazaaminopterin (1) and 5,10-dideaza-5,6,7,8-tetrahydroaminopterin (2) are described. These compounds exhibit significant in vivo activity against L1210 leukemia that is comparable to that observed with methotrexate.

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Year:  1985        PMID: 4009615     DOI: 10.1021/jm00145a012

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


  16 in total

1.  Structures of apo and complexed Escherichia coli glycinamide ribonucleotide transformylase.

Authors:  R J Almassy; C A Janson; C C Kan; Z Hostomska
Journal:  Proc Natl Acad Sci U S A       Date:  1992-07-01       Impact factor: 11.205

2.  Synthesis and biological activity of a novel series of 6-substituted thieno[2,3-d]pyrimidine antifolate inhibitors of purine biosynthesis with selectivity for high affinity folate receptors over the reduced folate carrier and proton-coupled folate transporter for cellular entry.

Authors:  Yijun Deng; Xilin Zhou; Sita Kugel Desmoulin; Jianmei Wu; Christina Cherian; Zhanjun Hou; Larry H Matherly; Aleem Gangjee
Journal:  J Med Chem       Date:  2009-05-14       Impact factor: 7.446

3.  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 4.  The major facilitative folate transporters solute carrier 19A1 and solute carrier 46A1: biology and role in antifolate chemotherapy of cancer.

Authors:  Larry H Matherly; Mike R Wilson; Zhanjun Hou
Journal:  Drug Metab Dispos       Date:  2014-01-06       Impact factor: 3.922

5.  Induction of HL-60 leukemia cell differentiation by tetrahydrofolate inhibitors of de novo purine nucleotide biosynthesis.

Authors:  J A Sokoloski; G P Beardsley; A C Sartorelli
Journal:  Cancer Chemother Pharmacol       Date:  1991       Impact factor: 3.333

6.  Synthesis, biological, and antitumor activity of a highly potent 6-substituted pyrrolo[2,3-d]pyrimidine thienoyl antifolate inhibitor with proton-coupled folate transporter and folate receptor selectivity over the reduced folate carrier that inhibits β-glycinamide ribonucleotide formyltransferase.

Authors:  Lei Wang; Sita Kugel Desmoulin; Christina Cherian; Lisa Polin; Kathryn White; Juiwanna Kushner; Andreas Fulterer; Min-Hwang Chang; Shermaine Mitchell-Ryan; Mark Stout; Michael F Romero; Zhanjun Hou; Larry H Matherly; Aleem Gangjee
Journal:  J Med Chem       Date:  2011-09-22       Impact factor: 7.446

7.  Synergy between 5,10-dideaza-5,6,7,8-tetrahydrofolic acid and methotrexate in mice bearing L1210 tumors.

Authors:  K Ferguson; D Boschelli; P Hoffman; A Oronsky; J Whiteley; S Webber; J Galivan; J Freishiem; J Hynes; S S Kerwar
Journal:  Cancer Chemother Pharmacol       Date:  1989       Impact factor: 3.333

8.  Protein preparation, crystallization and preliminary crystallographic studies of Bacillus subtilis glycinamide ribonucleotide transformylase.

Authors:  Yu-He Liang; Xiang-Yu Liu; Juan Wang; Lan-Fen Li
Journal:  Acta Crystallogr Sect F Struct Biol Cryst Commun       Date:  2009-06-27

9.  Biological and structural evaluation of 10R- and 10S-methylthio-DDACTHF reveals a new role for sulfur in inhibition of glycinamide ribonucleotide transformylase.

Authors:  Stephen Connelly; Jessica K DeMartino; Dale L Boger; Ian A Wilson
Journal:  Biochemistry       Date:  2013-07-19       Impact factor: 3.162

10.  Asymmetric synthesis of inhibitors of glycinamide ribonucleotide transformylase.

Authors:  Jessica K DeMartino; Inkyu Hwang; Stephen Connelly; Ian A Wilson; Dale L Boger
Journal:  J Med Chem       Date:  2008-08-08       Impact factor: 7.446

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