磺酸纳米孔硅（SBA-Pr-SO3H）促进的吡喃并[2,3-d]-嘧啶二酮衍生物的三组分合成及其对接和脲酶抑制活性。

BACKGROUND

A straightforward and efficient method for the synthesis of pyrano[2,3-d]pyrimidine diones derivatives from the reaction of barbituric acid, malononitrile and various aromatic aldehydes using SBA-Pr-SO3H as a nanocatalyst is reported.

RESULTS

Reactions proceed with high efficiency under solvent free conditions. Urease inhibitory activity of pyrano[2,3-d]pyrimidine diones derivatives were tested against Jack bean urease using phenol red method. Three compounds of 4a, 4d and 4l were not active in urease inhibition test, but compound 4a displayed slight urease activation properties. Compounds 4b, 4k, 4f, 4e, 4j, 4g and 4c with hydrophobic substitutes on phenyl ring, showed good inhibitory activity (19.45-279.14 μM).

DISCUSSION

The compounds with electron donating group and higher hydrophobic interaction with active site of enzyme prevents hydrolysis of substrate. Electron withdrawing groups such as nitro at different position and meta-methoxy reduced urease inhibitory activity. Substitution of both hydrogen of barbituric acid with methyl group will convert inhibitor to activator.

背景

本文报道了一种简便高效的方法，使用 SBA-Pr-SO3H 纳米催化剂，由巴比妥酸、丙二腈和各种芳香醛反应合成吡喃并[2,3-d]嘧啶二酮衍生物。

结果

在无溶剂条件下，反应高效进行。采用苯酚红法测定吡喃并[2,3-d]嘧啶二酮衍生物对刀豆脲酶的抑制活性。化合物 4a、4d 和 4l 对脲酶抑制试验无活性，但化合物 4a 显示出轻微的脲酶激活特性。具有苯环上疏水取代基的化合物 4b、4k、4f、4e、4j、4g 和 4c 表现出良好的抑制活性（19.45-279.14 μM）。