5-isopropyl-2,3,4-trimethoxybenzoic acid | 913961-20-3

• 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: 5-isopropyl-2,3,4-trimethoxybenzoic acid
• 英文别名: 2,3,4-Trimethoxy-5-propan-2-ylbenzoic acid；2,3,4-trimethoxy-5-propan-2-ylbenzoic acid
• CAS: 913961-20-3
• 化学式: C₁₃H₁₈O₅
• 分子量: 254.283
• InChiKey: YMIMHZNPJSCWIQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-isopropyl-2,3,4-trimethoxybenzoic acid 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 9.0h， 生成 (3,4-dihydroisoquinolin-2(1H)-yl)(5-isopropyl-2,3,4-trimethoxyphenyl)methanone
  参考文献：
  名称：

  Pyrogallol-Based Molecules as Potent Inhibitors of the Antiapoptotic Bcl-2 Proteins

  摘要：

  We report herein a new class of small-molecule inhibitors of antiapoptotic Bcl-2 proteins. The most potent compound, 7, binds to Bcl-2, Bcl-xL, and Mcl-1 proteins with K-i of 110, 638, and 150 nM, respectively. Compound 7 is highly effective in induction of cell death in breast cancer cells with high levels of Bcl-2, Bcl-xL, and Mcl-1 proteins and represents a promising lead compound for the design of new anticancer drugs.

  DOI：

  10.1021/jm061400l
• 作为产物：
  描述：

  1-isopropenyl-2,3,4-trimethoxybenzene 在 palladium on activated charcoal 六甲基磷酰三胺 、 氢气 、 叔丁基锂 作用下， 以 四氢呋喃 、 乙醇 、 正戊烷 为溶剂， -78.0 ℃ 、206.84 kPa 条件下， 反应 4.67h， 生成 5-isopropyl-2,3,4-trimethoxybenzoic acid
  参考文献：
  名称：

  Pyrogallol-Based Molecules as Potent Inhibitors of the Antiapoptotic Bcl-2 Proteins

  摘要：

  We report herein a new class of small-molecule inhibitors of antiapoptotic Bcl-2 proteins. The most potent compound, 7, binds to Bcl-2, Bcl-xL, and Mcl-1 proteins with K-i of 110, 638, and 150 nM, respectively. Compound 7 is highly effective in induction of cell death in breast cancer cells with high levels of Bcl-2, Bcl-xL, and Mcl-1 proteins and represents a promising lead compound for the design of new anticancer drugs.

  DOI：

  10.1021/jm061400l

文献信息

• Novel Hsp90 Inhibitor
  申请人：Kuramochi Hiroshi

  公开号：US20080269218A1

  公开（公告）日：2008-10-30

  Disclosed is a triazole derivative represented by the general formula (1) below or a pharmacologically acceptable salt thereof. Also disclosed are a prodrug of such a triazole derivative and an HSP90 inhibitor containing any one of them as an active constituent. (1) (In the formula, X represents a halogen atom, an optionally substituted alkyl group, an optionally substituted alkenyl group or the like; Y represents a mercapto group, a hydroxyl group, an optionally substituted sulfonyl group, an optionally substituted amino group or the like; and R represents an optionally substituted aryl or amino group or the like.)

  本发明公开了一种由下述通式（1）表示的三唑衍生物或其药物可接受的盐。还公开了这种三唑衍生物的前药和含有其中任何一种作为活性成分的HSP90抑制剂。(1) （在公式中，X代表卤素原子，可选取代的烷基，可选取代的烯基或类似物; Y代表巯基，羟基，可选取代的磺酰基，可选取代的氨基或类似物; R代表可选取代的芳基或氨基或类似物。）
• Novel HSP90 Inhibitor
  申请人：NIPPON KAYAKU KABUSHIKI KAISHA

  公开号：US20130116252A1

  公开（公告）日：2013-05-09

  Disclosed is a triazole derivative(s) represented by the general formula (1) below or a pharmacologically acceptable salt(s) thereof. Also disclosed are a prodrug(s) of such a triazole derivative(s) and an HSP90 inhibitor(s) containing any one of them as an active constituent. (1) (In the formula, X represents a halogen atom, an optionally substituted alkyl group, an optionally substituted alkynyl group or the like; Y represents a mercapto group, a hydroxyl group, an optionally substituted sulfonyl group, an optionally substituted amino group or the like; and R represents an optionally substituted aryl or alkyl group or the like.)

  本发明涉及一种由下式（1）表示的三唑衍生物或其药理学上可接受的盐。本发明还涉及此类三唑衍生物的前药以及含有其中任何一种作为活性成分的HSP90抑制剂。式中，X代表卤素原子，可选取代的烷基，可选取代的炔基或类似物；Y代表巯基，羟基，可选取代的磺酰基，可选取代的氨基或类似物；R代表可选取代的芳基或烷基或类似物。
• NOVEL HSP90 INHIBITOR
  申请人：NIPPON KAYAKU KABUSHIKI KAISHA

  公开号：EP1857446A1

  公开（公告）日：2007-11-21

  Disclosed is a triazole derivative represented by the general formula (1) below or a pharmacologically acceptable salt thereof. Also disclosed are a prodrug of such a triazole derivative and an HSP90 inhibitor containing any one of them as an active constituent. (1) (In the formula, X represents a halogen atom, an optionally substituted alkyl group, an optionally substituted alkenyl group or the like; Y represents a mercapto group, a hydroxyl group, an optionally substituted sulfonyl group, an optionally substituted amino group or the like; and R represents an optionally substituted aryl or amino group or the like.)

  本发明公开了如下通式(1)所代表的三唑衍生物或其药理学上可接受的盐。还公开了这种三唑衍生物的原药和含有其中任一种作为活性成分的 HSP90 抑制剂。(1)（式中，X代表卤原子、任选取代的烷基、任选取代的烯基或类似物；Y代表巯基、羟基、任选取代的磺酰基、任选取代的氨基或类似物；R代表任选取代的芳基或氨基或类似物）。
• Derivatives of 3-(2,4-dihydroxyphenyl)-1,2,4-triazole useful in the treatment of cancer
  申请人：NIPPON KAYAKU KABUSHIKI KAISHA

  公开号：EP1857446B1

  公开（公告）日：2013-05-01
• Structure-Based Design of Potent Small-Molecule Inhibitors of Anti-Apoptotic Bcl-2 Proteins
  作者：Guoping Wang、Zaneta Nikolovska-Coleska、Chao-Yie Yang、Renxiao Wang、Guozhi Tang、Jie Guo、Sanjeev Shangary、Su Qiu、Wei Gao、Dajun Yang、Jennifer Meagher、Jeanne Stuckey、Krzysztof Krajewski、Sheng Jiang、Peter P. Roller、Hatice Ozel Abaan、York Tomita、Shaomeng Wang

  DOI：10.1021/jm060460o

  日期：2006.10.1

  A structure-based approach was employed to design a new class of small-molecule inhibitors of Bcl-2. The most potent compound 5 (TW-37) binds to Bcl-2 with a K-i value of 290 nM and also to BclxL and Mcl-1 with high affinities. Compound 5 potently inhibits cell growth in PC-3 prostate cancer cells with an IC50 value of 200 nM and effectively induces apoptosis in a dose-dependent manner.