2-((2-hydroxyethyl)thio)benzoic acid | 58980-52-2

• 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-((2-hydroxyethyl)thio)benzoic acid
• 英文别名: 2-β-Hydroxyethylthio-benzoesaeure；2-(2-hydroxy-ethylsulfanyl)-benzoic acid；2-(2-Hydroxy-aethylmercapto)-benzoesaeure；2-[(2-Hydroxyethyl)sulfanyl]benzoic acid；2-(2-hydroxyethylsulfanyl)benzoic acid
• CAS: 58980-52-2
• 化学式: C₉H₁₀O₃S
• mdl: MFCD00020273
• 分子量: 198.243
• InChiKey: JCSPGCUGRGURES-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  82.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-((2-hydroxyethyl)thio)benzoic acid 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以81%的产率得到2,3-dihydro-5H-benzo[e][1,4]oxathiepin-5-one
  参考文献：
  名称：

  Cu-Mediated C–H Thioetherification of Arenes at Room Temperature

  摘要：

  Cu-mediated C-H thioetherification of arenes with ethylene sulfide has been developed using a readily removable directing group. The reaction proceeded at room temperature, and a variety of sensitive functional groups including chloro, bromo, and vinyl were well tolerated. The thiolated products could be converted to the seven-membered benzoxathiepinones derivatives by a sequence of hydrolysis-lactonization reactions.

  DOI：

  10.1021/acs.orglett.9b02120
• 作为产物：
  描述：

  2-((2-((2-(4,5-dihydrooxazol-2-yl)phenyl)carbamoyl)phenyl)thio)ethyl acetate 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以76%的产率得到2-((2-hydroxyethyl)thio)benzoic acid
  参考文献：
  名称：

  Cu-Mediated C–H Thioetherification of Arenes at Room Temperature

  摘要：

  Cu-mediated C-H thioetherification of arenes with ethylene sulfide has been developed using a readily removable directing group. The reaction proceeded at room temperature, and a variety of sensitive functional groups including chloro, bromo, and vinyl were well tolerated. The thiolated products could be converted to the seven-membered benzoxathiepinones derivatives by a sequence of hydrolysis-lactonization reactions.

  DOI：

  10.1021/acs.orglett.9b02120

文献信息

• Discovery and Structure−Activity Relationships of Imidazole-Containing Tetrahydrobenzodiazepine Inhibitors of Farnesyltransferase
  作者：Charles Z. Ding、Roberta Batorsky、Rajeev Bhide、Hannguang J. Chao、Young Cho、Saeho Chong、Johnni Gullo-Brown、Peng Guo、Soong Hoon Kim、Frank Lee、Katerina Leftheris、Arthur Miller、Toomas Mitt、Manorama Patel、Becky A. Penhallow、Carol Ricca、William C. Rose、Robert Schmidt、William A. Slusarchyk、Gregory Vite、Ning Yan、Veeraswamy Manne、John T. Hunt

  DOI：10.1021/jm990391w

  日期：1999.12.1

  4,5-Tetrahydro-1-(imidazol-4-ylalkyl)-1,4-benzodiazepines were found to be potent inhibitors of farnesyltransferase (FT). A hydrophobic substituent at the 4-position of the benzodiazepine, linked via a hydrogen bond acceptor, was important to enzyme inhibitory activity. An aryl ring at position 7 or a hydrophobic group linked to the 8-position through an amide, carbamate, or urea linkage was also important

  发现2,3,4,5-四氢-1-（咪唑-4-基烷基）-1,4-苯并二氮杂卓是法呢基转移酶（FT）的有效抑制剂。通过氢键受体连接的苯二氮杂卓的4位疏水取代基对酶抑制活性很重要。7位的芳基环或通过酰胺，氨基甲酸酯或脲键与8位连接的疏水基团对于有效抑制也很重要。2,3,4,5-四氢-1-（1H-咪唑-4-基甲基）-7-（4-吡啶基）-4- [2-（三氟罗甲氧基）苯甲酰基] -1H-1,4-苯并二氮杂（36）的FT IC（50）值为24 nM，在1.25 microM时产生Ras转化的NIH 3T3细胞85％的表型回复，并且EC（50）为160 nM，用于抑制软琼脂中锚定非依赖性生长H-Ras转化的Rat-1细胞的数量。
• [EN] ACYL PIPERAZINE DERIVATIVES AS TTX-S BLOCKERS<br/>[FR] DÉRIVÉS D'ACYLPIPÉRAZINE À TITRE DE BLOQUEURS DE TTX-S
  申请人：RAQUALIA PHARMA INC

  公开号：WO2012020567A1

  公开（公告）日：2012-02-16

  The present invention relates to acyl piperazine derivatives which have blocking activities of voltage gated sodium channels as the TTX-S channels, and which are useful in the treatment or prevention of disorders and diseases in which voltage gated sodium channels are involved. The invention also relates to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which voltage gated sodium channels are involved.

  本发明涉及酰基哌嗪衍生物，具有阻断电压门控钠通道（如TTX-S通道）活性的特性，可用于治疗或预防涉及电压门控钠通道的疾病和疾病。该发明还涉及包含这些化合物的药物组合物以及在预防或治疗涉及电压门控钠通道的疾病中使用这些化合物和组合物。
• Acyl Piperazine Derivatives as TTX-S Blockers
  申请人：Morita Mikiko

  公开号：US20130150356A1

  公开（公告）日：2013-06-13

  The present invention relates to acyl piperazine derivatives which have blocking activities of voltage gated sodium channels as the TTX-S channels, and which are useful in the treatment or prevention of disorders and diseases in which voltage gated sodium channels are involved. The invention also relates to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which voltage gated sodium channels are involved.

  本发明涉及酰基哌嗪衍生物，具有阻断电压门控钠通道（TTX-S通道）的活性，并且在治疗或预防涉及电压门控钠通道的疾病和疾病方面非常有用。本发明还涉及包含这些化合物的制药组合物以及在预防或治疗涉及电压门控钠通道的疾病中使用这些化合物和组合物的用途。
• 292. The rearrangement of o-hydroxysulphones. Part V
  作者：Frederick Galbraith、Samuel Smiles

  DOI：10.1039/jr9350001234

  日期：——
• Gilbert,J. et al., Bulletin de la Societe Chimique de France, 1975, p. 277 - 282
  作者：Gilbert,J. et al.

  DOI：——

  日期：——