2-methoxy-4-(3-trifluoromethyl-3H-diazirin-3-yl)-benzoic acid 2,5-dioxopyrrolidin-1-yl ester | 173949-59-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-methoxy-4-(3-trifluoromethyl-3H-diazirin-3-yl)-benzoic acid 2,5-dioxopyrrolidin-1-yl ester
• 英文别名: (2,5-Dioxopyrrolidin-1-yl) 2-methoxy-4-[3-(trifluoromethyl)diazirin-3-yl]benzoate
• CAS: 173949-59-2
• 化学式: C₁₄H₁₀F₃N₃O₅
• 分子量: 357.246
• InChiKey: PGLIEKOOTJRBMR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  97.6
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2-methoxy-4-(3-trifluoromethyl-3H-diazirin-3-yl)-benzoic acid 2,5-dioxopyrrolidin-1-yl ester 在 sodium hydroxide 、 三乙胺 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基乙酰胺 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 37.62h， 生成 [(3R,4S,5R,8S,9S,12R)-5,9-dihydroxy-4-methoxy-12-[(2S,3S,6R,8S,9R)-8-[(3S,4Z)-4-[2-[2-[[2-methoxy-4-[3-(trifluoromethyl)diazirin-3-yl]benzoyl]amino]ethylamino]-2-oxoethoxy]imino-3-methylpentyl]-3,9-dimethyl-1,7-dioxaspiro[5.5]undecan-2-yl]-2,8-dimethyl-7-oxotridecan-3-yl] (3R)-3-hydroxy-3-(4-methyl-2,5-dioxofuran-3-yl)propanoate
  参考文献：
  名称：

  Synthesis of photoaffinity probes of tautomycin

  摘要：

  Two types of photoaffinity: probe, which possesses a benzophenone or a diazirine photophore on the 2-position of tautomycin, were prepared in order to prove the details of binding site to PP1. These photoaffinity probes were designed on the basis of the structure-activity relationship; thus, the diacid moiety is indispensable. The selective introduction of photolabeling units on the 2-position of tautomycin was achieved through the 2-oxime of tautomycin diacid. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.12.053
• 作为产物：
  描述：

  2-甲氧基-4-[3-(三氟甲基)-3H-双吖丙啶-3-基]苯甲醛 在 吡啶 、 四丁基高锰酸胺盐 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 2-methoxy-4-(3-trifluoromethyl-3H-diazirin-3-yl)-benzoic acid 2,5-dioxopyrrolidin-1-yl ester
  参考文献：
  名称：

  Synthesis of photoaffinity probes of tautomycin

  摘要：

  Two types of photoaffinity: probe, which possesses a benzophenone or a diazirine photophore on the 2-position of tautomycin, were prepared in order to prove the details of binding site to PP1. These photoaffinity probes were designed on the basis of the structure-activity relationship; thus, the diacid moiety is indispensable. The selective introduction of photolabeling units on the 2-position of tautomycin was achieved through the 2-oxime of tautomycin diacid. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.12.053

文献信息

• Indolizine Derivatives as HIV-1 VIF-ElonginC Interaction Inhibitors
  作者：Wenlin Huang、Tao Zuo、Xiao Luo、Hongwei Jin、Zhenming Liu、Zhenjun Yang、Xianghui Yu、Liangren Zhang、Lihe Zhang

  DOI：10.1111/cbdd.12119

  日期：2013.6

  Compound 1 (VEC‐5) was identified as a potent small‐molecular HIV‐1 viron infectivity factor inhibitor that targets the viron infectivity factor–ElonginC interaction. A structure–activity relationship study was carried out to develop compounds with improved efficacy against HIV‐1 and 49 indolizine derivatives of three categories were designed and synthesized. We found that five compounds exhibited promising anti‐HIV‐1 activity, and the most active compound 2g had an IC50 value of 11.0 μm. These results provide new information to develop highly potent small‐molecule HIV‐1 viron infectivity factor inhibitors.
• Synthesis of photoaffinity probes of tautomycin
  作者：Masakuni Kurono、Aya Shimomura、Minoru Isobe

  DOI：10.1016/j.tet.2003.12.053

  日期：2004.2

  Two types of photoaffinity: probe, which possesses a benzophenone or a diazirine photophore on the 2-position of tautomycin, were prepared in order to prove the details of binding site to PP1. These photoaffinity probes were designed on the basis of the structure-activity relationship; thus, the diacid moiety is indispensable. The selective introduction of photolabeling units on the 2-position of tautomycin was achieved through the 2-oxime of tautomycin diacid. (C) 2004 Elsevier Ltd. All rights reserved.