1-(3-(5-allyl-5H-[1,2,4]triazino[5,6-b]indol-3-ylthio)propyl)-1H-benzo[d]imidazol-2(3H)-one | 442653-38-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1-(3-(5-allyl-5H-[1,2,4]triazino[5,6-b]indol-3-ylthio)propyl)-1H-benzo[d]imidazol-2(3H)-one
• 英文别名: 77074；1-(3-{[5-(prop-2-en-1-yl)-5H-[1,2,4]triazino[5,6-b]indol-3-yl]sulfanyl}propyl)-1,3-dihydro-2H-benzimidazol-2-one；3-[3-[(5-prop-2-enyl-[1,2,4]triazino[5,6-b]indol-3-yl)sulfanyl]propyl]-1H-benzimidazol-2-one
• CAS: 442653-38-5
• 化学式: C₂₂H₂₀N₆OS
• 分子量: 416.506
• InChiKey: CJYPAACHDZZHAQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(3-(5-allyl-5H-[1,2,4]triazino[5,6-b]indol-3-ylthio)propyl)-1H-benzo[d]imidazol-2(3H)-one 在 sodium tungstate (VI) dihydrate 、 苯膦酸 、 双氧水 、 三辛基甲基硫酸铵 作用下， 以 水 为溶剂， 反应 24.0h， 以53.1%的产率得到1-(3-(5-allyl-5H-[1,2,4]triazino[5,6-b]indol-3-ylsulfonyl)-propyl)-1H-benzo[d]imidazol-2(3H)-one
  参考文献：
  名称：

  Identification of triazinoindol-benzimidazolones as nanomolar inhibitors of the Mycobacterium tuberculosis enzyme TDP-6-deoxy-d-xylo-4-hexopyranosid-4-ulose 3,5-epimerase (RmlC)

  摘要：

  High-throughput screening of 201,368 compounds revealed that 1-(3-(5-ethyl-5H-[1,2,4]triazino[5,6-b]indol-3-ylthio)propyl)-1H-benzo[d]imidazol-2(3H)-one (SID 7975595) inhibited RmlC a TB cell wall biosynthetic enzyme. SID 7975595 acts as a competitive inhibitor of the enzyme's substrate and inhibits RmlC as a fast-on rate, fully reversible inhibitor. An analog of SID 7975595 had a K-i of 62 nM. Computer modeling showed that the binding of the tethered two-ringed system into the active site occurred at the thymidine binding region for one ring system and the sugar region for the other ring system. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.11.033
• 作为产物：
  描述：

  9-烯丙基-9H-1,3,4,9-四氮杂-芴-2-硫醇 、 1-(3-氯丙基)-1,3-二氢-2H-苯并咪唑-2-酮 在 potassium hydroxide 作用下， 以 水 为溶剂， 反应 26.0h， 以55.2%的产率得到1-(3-(5-allyl-5H-[1,2,4]triazino[5,6-b]indol-3-ylthio)propyl)-1H-benzo[d]imidazol-2(3H)-one
  参考文献：
  名称：

  Identification of triazinoindol-benzimidazolones as nanomolar inhibitors of the Mycobacterium tuberculosis enzyme TDP-6-deoxy-d-xylo-4-hexopyranosid-4-ulose 3,5-epimerase (RmlC)

  摘要：

  High-throughput screening of 201,368 compounds revealed that 1-(3-(5-ethyl-5H-[1,2,4]triazino[5,6-b]indol-3-ylthio)propyl)-1H-benzo[d]imidazol-2(3H)-one (SID 7975595) inhibited RmlC a TB cell wall biosynthetic enzyme. SID 7975595 acts as a competitive inhibitor of the enzyme's substrate and inhibits RmlC as a fast-on rate, fully reversible inhibitor. An analog of SID 7975595 had a K-i of 62 nM. Computer modeling showed that the binding of the tethered two-ringed system into the active site occurred at the thymidine binding region for one ring system and the sugar region for the other ring system. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.11.033

文献信息

• Identification of triazinoindol-benzimidazolones as nanomolar inhibitors of the Mycobacterium tuberculosis enzyme TDP-6-deoxy-d-xylo-4-hexopyranosid-4-ulose 3,5-epimerase (RmlC)
  作者：Sharmila Sivendran、Victoria Jones、Dianqing Sun、Yi Wang、Anna E. Grzegorzewicz、Michael S. Scherman、Andrew D. Napper、J. Andrew McCammon、Richard E. Lee、Scott L. Diamond、Michael McNeil

  DOI：10.1016/j.bmc.2009.11.033

  日期：2010.1

  High-throughput screening of 201,368 compounds revealed that 1-(3-(5-ethyl-5H-[1,2,4]triazino[5,6-b]indol-3-ylthio)propyl)-1H-benzo[d]imidazol-2(3H)-one (SID 7975595) inhibited RmlC a TB cell wall biosynthetic enzyme. SID 7975595 acts as a competitive inhibitor of the enzyme's substrate and inhibits RmlC as a fast-on rate, fully reversible inhibitor. An analog of SID 7975595 had a K-i of 62 nM. Computer modeling showed that the binding of the tethered two-ringed system into the active site occurred at the thymidine binding region for one ring system and the sugar region for the other ring system. (C) 2009 Elsevier Ltd. All rights reserved.