1-methoxymethyl-6-chlorouracil | 228396-40-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1-methoxymethyl-6-chlorouracil
• 英文别名: 6-chloro-1-methoxymethyluracil；6-Chloro-1-(methoxymethyl)pyrimidine-2,4-dione
• CAS: 228396-40-5
• 化学式: C₆H₇ClN₂O₃
• 分子量: 190.586
• InChiKey: HXXBAROFEITNNT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-methoxymethyl-6-chlorouracil 在 偶氮二甲酰胺 、 B-溴代邻苯二氧硼烷 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 2-[6-Chloro-3-[(3,5-dimethylphenyl)methyl]-2,4-dioxo-pyrimidin-1-yl]acetonitrile
  参考文献：
  名称：

  Synthesis and evaluation of novel 3-(3,5-dimethylbenzyl)uracil analogs as potential anti-HIV-1 agents

  摘要：

  A novel series of uracil derivatives with a 3,5-dimethylbenzyl group at the N-3-position were synthesized and evaluated as non-nucleoside HIV-1 reverse transcriptase inhibitors. Some of these compounds showed good-to-moderate activity with EC50 values in the submicromolar range. Among them, compound 10c showed significant potency against HIV-1 activity with an EC50 value of 0.03 mu M and a high selectivity index of 2863. Preliminary structure-activity relationships and molecular modeling analyses were used to explore the major interactions between HIV-1 reverse transcriptase and the potent inhibitor 10c, which may serve as an important lead for further optimization. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.06.061
• 作为产物：
  描述：

  6-氯尿嘧啶 、 氯甲基甲基醚 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以90%的产率得到1-methoxymethyl-6-chlorouracil
  参考文献：
  名称：

  Synthesis and evaluation of novel 3-(3,5-dimethylbenzyl)uracil analogs as potential anti-HIV-1 agents

  摘要：

  A novel series of uracil derivatives with a 3,5-dimethylbenzyl group at the N-3-position were synthesized and evaluated as non-nucleoside HIV-1 reverse transcriptase inhibitors. Some of these compounds showed good-to-moderate activity with EC50 values in the submicromolar range. Among them, compound 10c showed significant potency against HIV-1 activity with an EC50 value of 0.03 mu M and a high selectivity index of 2863. Preliminary structure-activity relationships and molecular modeling analyses were used to explore the major interactions between HIV-1 reverse transcriptase and the potent inhibitor 10c, which may serve as an important lead for further optimization. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.06.061

文献信息

• Synthesis and Biochemical Evaluation of Bis(6,7-dimethyl-8-<scp>d</scp>-ribityllumazines) as Potential Bisubstrate Analogue Inhibitors of Riboflavin Synthase
  作者：Mark Cushman、Farahnaz Mavandadi、Donglai Yang、Karl Kugelbrey、Klaus Kis、Adelbert Bacher

  DOI：10.1021/jo9821731

  日期：1999.6.1

  The reaction catalyzed by riboflavin synthase utilizes two identical 6,7-dimethyl-8-n-ribityllumazine substrate molecules. Three bis(6,7-dimethyl-8-D-ribityllumazines) were, therefore, synthesized in which the two lumazine moieties were connected through their N-3 nitrogen atoms by polymethylene linker chains containing three, four, and five carbon atoms. The compounds with three and five carbon linkers were found to be very weak inhibitors of riboflavin synthase, having inhibition constants of 320 and >1000 mu M, respectively. In contrast, the bis(lumazine) with a four-carbon linker was much more potent, with an inhibition constant of 37 mu M. These results have potential implications for understanding the distance between the donor and acceptor sites of riboflavin synthase and the orientations of the two 6,7-dimethyl-8-D-ribityllumazine substrate molecules which occupy these two sites.
• [DE] INHIBITOREN DER BIOSYNTHESE VON VITAMIN B2 UND VERFAHREN ZU IHRER HERSTELLUNG<br/>[EN] INHIBITORS FOR THE BIOSYNTHESIS OF VITAMIN B2 AND METHOD FOR PRODUCING SAME<br/>[FR] INHIBITEURS POUR LA BIOSYNTHESE DE VITAMINE B2 ET LEUR PROCEDE DE PRODUCTION
  申请人：BACHER ADELBERT

  公开号：WO2000044727A1

  公开（公告）日：2000-08-03

  Es wird eine Klasse von Inhibitoren der allgemeinen Formeln (I, II, III und IV) für die Biosynthese von Vitamin B2 beschrieben, sowie ein Verfahren zu ihrer Herstellung. Die Inhibitoren sind wirksam zur Inhibierung der Lumazinsynthase und/oder der Riboflavinsynthase. Sie kommen als Wirkstoffe von Herbiziden, Fungiziden, oder Bakteriziden in Frage.
• Synthesis and evaluation of novel 3-(3,5-dimethylbenzyl)uracil analogs as potential anti-HIV-1 agents
  作者：Norikazu Sakakibara、Takayuki Hamasaki、Masanori Baba、Yosuke Demizu、Masaaki Kurihara、Kohji Irie、Masatoshi Iwai、Eriko Asada、Yoshihisa Kato、Tokumi Maruyama

  DOI：10.1016/j.bmc.2013.06.061

  日期：2013.9

  A novel series of uracil derivatives with a 3,5-dimethylbenzyl group at the N-3-position were synthesized and evaluated as non-nucleoside HIV-1 reverse transcriptase inhibitors. Some of these compounds showed good-to-moderate activity with EC50 values in the submicromolar range. Among them, compound 10c showed significant potency against HIV-1 activity with an EC50 value of 0.03 mu M and a high selectivity index of 2863. Preliminary structure-activity relationships and molecular modeling analyses were used to explore the major interactions between HIV-1 reverse transcriptase and the potent inhibitor 10c, which may serve as an important lead for further optimization. (C) 2013 Elsevier Ltd. All rights reserved.