Synthesis of pseudocofactor analogs as potential inhibitors of the folate enzymes

…, JD Rose, RD Elliott, JH Montgomery

Index: Temple, Carroll; Bennett, L. Lee; Rose, Jerry D.; Elliott, Robert D.; Montgomery, John A.; Mangum, John H. Journal of Medicinal Chemistry, 1982 , vol. 25, # 2 p. 161 - 166

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Citation Number: 23

Abstract

Reaction of 5, 6, 7, 8-tetr&ydrofolic acid (THF, 7) with phosgene, thiophosgene, and cyanogen bromide gave the bridged derivatives, 5, 10-(CO)-THF (8), 5, 10-(CS)-THF (9), and 5, 10-(C== NH)-THF (ll), respectively. Catalytic hydrogenation of 10-(chloroacety1) folic acid (2) gave 5, 10-(CH2CO)-THF (12). A similar reaction with 10-(3-chloropropionyl) folic acid (3) gave 10-(CICHzCHzCO)-THF (14) rather than 5, lO-(CHzCHzCO)-THF (13). In the ...