methyl 5-chloro-2,3-dihydrobenzothiophene-3-carboxylate | 93670-23-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: methyl 5-chloro-2,3-dihydrobenzothiophene-3-carboxylate
• 英文别名: methyl 5-chloro-2,3-dihydro-1-benzothiophene-3-carboxylate
• CAS: 93670-23-6
• 化学式: C₁₀H₉ClO₂S
• 分子量: 228.699
• InChiKey: VCQSOFGASNIUEC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 5-chloro-2,3-dihydrobenzothiophene-3-carboxylate 在 三氯化铝 、 sodium ethanolate 、 sodium carbonate 、 间氯过氧苯甲酸 作用下， 以 二硫化碳 、 乙醇 、 二氯甲烷 为溶剂， 反应 77.5h， 生成 7-benzoyl-5-chloro-2,3-dihydro-1,1-dioxobenzothiophene-3-carboxylic acid
  参考文献：
  名称：

  7-Aroyl-2,3-dihydrobenzo[b]furan-3-carboxylic acids and 7-benzoyl-2,3-dihydrobenzo[b]thiophene-3-carboxylic acids as analgesic agents

  摘要：

  The synthesis of a series of 7-aroyl-2,3-dihydrobenzo[b]furan-3-carboxylic acids and 7-benzoyl-2,3-dihydrobenzo[b]thiophene-3-carboxylic acids is described. The isomeric 4-benzoyl-1,3-dihydrobenzo[c]furan-1-carboxylic acid was also prepared. Compounds were evaluated for analgesic activity in the mouse phenyl-p-quinone-induced writhing test. Selected compounds were tested for their ability to produce gastric damage in fasted mice and for inhibition of prostaglandin synthetase activity in vitro. Zomepirac was used as a reference. Structure-activity relationships are discussed. One of the compounds, 7-benzoyl-5-chloro-2,3-dihydrobenzo[b]furan-3-carboxylic acid (2c), combined potent analgesic activity with low gastric irritancy.

  DOI：

  10.1021/jm00156a004
• 作为产物：
  描述：

  methyl 5-chlorobenzothiophene-3-carboxylate 在 甲醇 、 magnesium 作用下， 生成 methyl 5-chloro-2,3-dihydrobenzothiophene-3-carboxylate
  参考文献：
  名称：

  7-Aroyl-2,3-dihydrobenzo[b]furan-3-carboxylic acids and 7-benzoyl-2,3-dihydrobenzo[b]thiophene-3-carboxylic acids as analgesic agents

  摘要：

  The synthesis of a series of 7-aroyl-2,3-dihydrobenzo[b]furan-3-carboxylic acids and 7-benzoyl-2,3-dihydrobenzo[b]thiophene-3-carboxylic acids is described. The isomeric 4-benzoyl-1,3-dihydrobenzo[c]furan-1-carboxylic acid was also prepared. Compounds were evaluated for analgesic activity in the mouse phenyl-p-quinone-induced writhing test. Selected compounds were tested for their ability to produce gastric damage in fasted mice and for inhibition of prostaglandin synthetase activity in vitro. Zomepirac was used as a reference. Structure-activity relationships are discussed. One of the compounds, 7-benzoyl-5-chloro-2,3-dihydrobenzo[b]furan-3-carboxylic acid (2c), combined potent analgesic activity with low gastric irritancy.

  DOI：

  10.1021/jm00156a004

文献信息

• Benzofuran and benzothiophene-carboxylic-acid derivatives
  申请人：BEECHAM GROUP PLC

  公开号：EP0117675A1

  公开（公告）日：1984-09-05

  Compounds of formula (I): wherein: Ar is phenyl optionally substituted in the o-, m-, or p-position by C1-4. alkyl, C1-4 alkoxy, trifluoromethyl, bromo, chloro or fluoro, pyrryl optionally N-substituted by C1-4 alkyl, 2-furyl or 2-thienyl either optionally substituted in the 3-, 4- or 5-position by methyl, chloro or bromo, or 3-furyl or 3-thienyl; X is oxygen, sulphur, sulphoxide or sulphone, Y is methylene, R1 and R3 are hydrogen or C1-4 alkyl, and R2 is hydrogen, C1-4 alkyl, fluoro, chloro or bromo, or X is methylene, Y is oxygen, R1 and R3 are both hydrogen, and R2 is hydrogen, fluoro, chloro or bromo; and R4 is hydrogen or C1-4 alkyl, or a salt thereof, have analgesic and/or anti-inflammatory activity.

  式(I)化合物： 其中 Ar 是在 o、m 或 p 位任选被 C1-4 烷基、C1-4 烷氧基、三氟甲基、溴、氯或氟取代的苯基、 由 C1-4 烷基任选 N 取代的吡咯基、 在 3-、4-或 5-位任选被甲基、氯或溴取代的 2-呋喃基或 2-噻吩基，或 3-呋喃基或 3-噻吩基； X 是氧、硫、亚砜或砜，Y 是亚甲基，R1 和 R3 是氢或 C1-4 烷基，R2 是氢、C1-4 烷基、氟、氯或溴，或 X 是亚甲基，Y 是氧，R1 和 R3 都是氢，R2 是氢、氟、氯或溴；以及 R4 是氢或 C1-4 烷基，或其盐，具有镇痛和/或消炎活性。
• BOYLE E. A.; MANGAN F. R.; MARKWELL R. E.; SMITH S. A.; THOMSON M. J.; WA+, J. MED. CHEM., 29,(1986) N 6, 894-898
  作者：BOYLE E. A.、 MANGAN F. R.、 MARKWELL R. E.、 SMITH S. A.、 THOMSON M. J.、 WA+

  DOI：——

  日期：——
• US4548948A
  申请人：——

  公开号：US4548948A

  公开（公告）日：1985-10-22