5-Isopropyl-salicylsaeure-methylester | 87188-65-6

• 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-salicylsaeure-methylester
• 英文别名: 2-hydroxy-5-isopropyl-benzoic acid methyl ester；2-Hydroxy-5-isopropyl-benzoesaeure-methylester；Methyl 2-hydroxy-5-isopropylbenzoate；methyl 2-hydroxy-5-propan-2-ylbenzoate
• CAS: 87188-65-6
• 化学式: C₁₁H₁₄O₃
• mdl: MFCD24392132
• 分子量: 194.23
• InChiKey: QTCPFTFVORQDGB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-Isopropyl-salicylsaeure-methylester 在 sodium hydroxide 作用下， 生成 2-羟基-5-异丙基苯甲酸
  参考文献：
  名称：

  ORGANIC REACTIONS WITH BORON FLUORIDE. XVII.^* REARRANGEMENT OF ALKYL SALICYLATES AND THE REACTION OF ALCOHOLS WITH SALICYLIC ACID

  摘要：

  DOI：

  10.1021/jo01226a007
• 作为产物：
  描述：

  柳酸丙酯 生成 5-Isopropyl-salicylsaeure-methylester
  参考文献：
  名称：

  ORGANIC REACTIONS WITH BORON FLUORIDE. XVII.^* REARRANGEMENT OF ALKYL SALICYLATES AND THE REACTION OF ALCOHOLS WITH SALICYLIC ACID

  摘要：

  DOI：

  10.1021/jo01226a007

文献信息

• Spirocyclopropane compounds. III. Synthesis of spiro(benzofuran-2(3H),1'-cyclopropan)-3-ones for evaluation as gastric antisecretory and antiulcer agents.
  作者：MITSURU KAWADA、MASAZUMI WATANABE、KAYOKO OKAMOTO、HIROSADA SUGIHARA、TAKEO HIRATA、YOSHITAKA MAKI、ISUKE IMADA、YASUSHI SANNO

  DOI：10.1248/cpb.32.3532

  日期：——

  Spiro [benzofuran-2 (3H), 1'-cyclopropan]-3-one (VI-1) and its derivatives (VI-2-VI-75) were synthesized in the same manner as described previously for the synthesis of spiro [cyclopropane-1, 2'-[2H] indol]-3'(1'H)-ones (I). These spiro [benzofuran-2 (3H), 1'-cyclopropan]-3-ones were evaluated for gastric antisecretory activity and protective activity against lesions induced by water-immersion restraint stress in the rat. The most potent antiulcer compounds (VI-17 and VI-55) were obtained by the introduction of an acetyl or dimethylamino group at the 5-position on the benzene ring. The most interesting member of the series, 5-acetylspiro [benzofuran-2 (3H), 1'-cyclopropan]-3-one (VI-17, AG-629), was selected as a candidate for clinical studies.

  苯并呋喃-2(3H),1'-环丙烷]-3-酮（VI-1）及其衍生物（VI-2至VI-75）按照之前合成螺[环丙烷-1,2'-[2H]吲哚]-3'(1'H)-酮（I）的方法合成了。这些螺[苯并呋喃-2(3H),1'-环丙烷]-3-酮被评估了其抗胃液分泌活性和对大鼠水浸束缚应激诱导的损伤的保护活性。通过在苯环的5位引入乙酰基或二甲氨基，获得了最具效力的抗溃疡化合物（VI-17和VI-55）。该系列中最有趣的成员，5-乙酰基螺[苯并呋喃-2(3H),1'-环丙烷]-3-酮（VI-17，AG-629），被选为临床研究的候选药物。
• The discovery of fluoropyridine-based inhibitors of the Factor VIIa/TF complex
  作者：Jeffrey T. Kohrt、Kevin J. Filipski、Wayne L. Cody、Cuiman Cai、Danette A. Dudley、Chad A. Van Huis、J. Adam Willardsen、Stephen T. Rapundalo、Kamlai Saiya-Cork、Robert J. Leadley、Lakshmi Narasimhan、Erli Zhang、Marc Whitlow、Marc Adler、Kirk McLean、Yuo-Ling Chou、Cecile McKnight、Damian O. Arnaiz、Kenneth J. Shaw、David R. Light、Jeremy J. Edmunds

  DOI：10.1016/j.bmcl.2005.07.059

  日期：2005.11

  The activated Factor VII/tissue factor complex (FVIIa/TF) plays a key role in the formation of blood clots. Inhibition of this complex may lead to new antithrombotic drugs. An X-ray crystal structure of a fluoropyridine-based FVIIa/TF inhibitor bound in the active site of the enzyme complex suggested that incorporation of substitution at the 5-position of the hydroxybenzoic acid side chain could lead to the formation of more potent inhibitors through interactions with the S1'/S2' pocket.
• KAWADA, MITSURU;WATANABE, MASAZUMI;OKAMOTO, KAYOKO;SUGIHARA, HIROSADA;HRA+, CHEM. AND PHARM. BULL., 1984, 32, N 9, 3532-3550
  作者：KAWADA, MITSURU、WATANABE, MASAZUMI、OKAMOTO, KAYOKO、SUGIHARA, HIROSADA、HRA+

  DOI：——

  日期：——