2-methyl-(4-oxo-4,5,6,7-tetrahydrobenzo[b]thiophen-5-yl)acetic acid | 119291-92-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-methyl-(4-oxo-4,5,6,7-tetrahydrobenzo[b]thiophen-5-yl)acetic acid
• 英文别名: 2-(2-methyl-4-oxo-6,7-dihydro-5H-1-benzothiophen-5-yl)acetic acid
• CAS: 119291-92-8
• 化学式: C₁₁H₁₂O₃S
• 分子量: 224.28
• InChiKey: NADJHWZEBYYYAY-UHFFFAOYSA-N

物化性质

• 沸点：
  442.1±33.0 °C(Predicted)
• 密度：
  1.313±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  82.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-methyl-(4-oxo-4,5,6,7-tetrahydrobenzo[b]thiophen-5-yl)acetic acid 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以86%的产率得到8-methyl-4,4a,5,6-tetrahydrothieno[2,3-h]cinnolin-3(2H)-one
  参考文献：
  名称：

  新型噻吩并nnolinone衍生物的合成和醛糖还原酶抑制活性。

  摘要：

  合成了一系列新颖的四氢噻吩并[2,3-h] cinnolinone衍生物，并在体外评估了其抑制醛糖还原酶（ALR2）的能力，醛糖还原酶是一种涉及糖尿病并发症出现的酶。化合物2e和2j具有显着的抑制作用，IC（50）分别为7.6和18 microM。这些化合物掺入了有效的药效基团，用于醛糖还原酶抑制活性，其特征是噻吩并nnolinone模板通过五亚甲基间隔基连接到羧基上。

  DOI：

  10.1016/j.ejps.2003.12.005
• 作为产物：
  描述：

  2-methyl-6,7-dihydrobenzo[b]thiophene-4(5H)-one 在 盐酸 作用下， 以 甲醇 、 水 、 溶剂黄146 为溶剂， 反应 11.5h， 生成 2-methyl-(4-oxo-4,5,6,7-tetrahydrobenzo[b]thiophen-5-yl)acetic acid
  参考文献：
  名称：

  Synthesis and evaluation of novel 2-aryl-2,5,6,7-tetrahydro-3H-thieno [2′,3′:6,7]cyclohepta[1,2-c]pyridazin-3-ones and 2-aryl-5, 6-dihydrothieno[2,3-h]cinnolin-3(2H)-ones as anxiolytics

  摘要：

  A series of 2-aryl-2,5,6,7-tetrahydro-3H-thieno[2',3':6,7]cyclohepta[1,2-c]pyridazin-3-ones and 2-aryl-5,6-dihydrothieno[2,3-h]cinnolin-3(2H)-ones were synthesized and evaluated for their affinity to benzodiazepine receptors (BZRs) in the excised brain of rats and also for their intrinsic efficacy in augmentation of the gamma-aminobutyric acid-induced chloride currents in the dissociated sensory neurons of frogs. The synthesized compounds showed a high affinity to BZRs. In these compounds, the substituents at the 2-position and at either the 8- or the 9-position and the ring size of the condensed ring affected the biological activity of the compounds. Thus, an introduction of 4-methyl- or 4-chloro-substitute phenyl ring into the 2-position, an introduction of methyl or ethyl into either the 8- or the 9-position, and an expansion of the 6-membered condensed ring to a 7-membered ring brought about a continuous shift of compounds from inverse to full agonists. Among the synthesized compounds, 8-(1 hydroxyethyl)-2-(4-methylphenyl)-5,6-dihydrothieno[2,3-h]cinnolin-3(2H)-one which can be classified as a BZR partial agonist, was found to exhibit an anxio-selective feature.

  DOI：

  10.1016/s0223-5234(97)83286-2

文献信息

• THIENOCINNOLINE COMPOUNDS AND THEIR MEDICINAL APPLICATION
  申请人：Yoshitomi Pharmaceutical Industries, Ltd.

  公开号：EP0308515A1

  公开（公告）日：1989-03-29

  Thienocinnoline compounds represented by general for- (wherein R represents hydrogen, halogen or lower alkyl, Ar represents aryl, heteroaryl, or aryl or heteroaryl having at least one substituent selected from the group consisting of halogen, lower alkyl, lower alkoxy, nitro, amino, hydroxy, trifluoromethyl and lower alkanoylamino, and between 5a-position and 6-position represents either a single or a double bond) useful as anti-anxious agents, amnesia treating agents, brain function activating agents, anti-dement agents or bioprotection accelerating agents.

  由以下通式表示的噻吩噌啉化合物 (其中 R 代表氢、卤素或低级烷基，Ar 代表芳基、杂芳基，或芳基或杂芳基具有至少一个选自卤素、低级烷基、低级烷氧基、硝基、氨基、羟基、三氟甲基和低级烷酰氨基组成的取代基，且 5a 位和 6 位之间代表单键或双键）的噻吩噌啉化合物，可用作抗焦虑剂、健忘治疗剂、脑功能激活剂、抗痴呆剂或生物保护加速剂。
• US4965264A
  申请人：——

  公开号：US4965264A

  公开（公告）日：1990-10-23
• Synthesis and evaluation of novel 2-aryl-2,5,6,7-tetrahydro-3H-thieno [2′,3′:6,7]cyclohepta[1,2-c]pyridazin-3-ones and 2-aryl-5, 6-dihydrothieno[2,3-h]cinnolin-3(2H)-ones as anxiolytics
  作者：H Tanaka、S Kirihara、H Yasumatsu、T Yakushiji、T Nakao

  DOI：10.1016/s0223-5234(97)83286-2

  日期：1997.7

  A series of 2-aryl-2,5,6,7-tetrahydro-3H-thieno[2',3':6,7]cyclohepta[1,2-c]pyridazin-3-ones and 2-aryl-5,6-dihydrothieno[2,3-h]cinnolin-3(2H)-ones were synthesized and evaluated for their affinity to benzodiazepine receptors (BZRs) in the excised brain of rats and also for their intrinsic efficacy in augmentation of the gamma-aminobutyric acid-induced chloride currents in the dissociated sensory neurons of frogs. The synthesized compounds showed a high affinity to BZRs. In these compounds, the substituents at the 2-position and at either the 8- or the 9-position and the ring size of the condensed ring affected the biological activity of the compounds. Thus, an introduction of 4-methyl- or 4-chloro-substitute phenyl ring into the 2-position, an introduction of methyl or ethyl into either the 8- or the 9-position, and an expansion of the 6-membered condensed ring to a 7-membered ring brought about a continuous shift of compounds from inverse to full agonists. Among the synthesized compounds, 8-(1 hydroxyethyl)-2-(4-methylphenyl)-5,6-dihydrothieno[2,3-h]cinnolin-3(2H)-one which can be classified as a BZR partial agonist, was found to exhibit an anxio-selective feature.
• Synthesis and aldose reductase inhibitory activities of novel thienocinnolinone derivatives
  作者：A Pau、B Asproni、G Boatto、G.E Grella、P De Caprariis、L Costantino、G.A Pinna

  DOI：10.1016/j.ejps.2003.12.005

  日期：2004.3

  tetrahydrothieno[2,3-h]cinnolinone derivatives were synthesized and evaluated in vitro for their ability to inhibit aldose reductase (ALR2), an enzyme involved in the appearance of diabetic complications. Compounds 2e and 2j exert a remarkable inhibitory effect, with IC(50) of 7.6 and 18 microM, respectively. These compounds incorporate a valid pharmacophore for aldose reductase inhibitory activity represented by a

  合成了一系列新颖的四氢噻吩并[2,3-h] cinnolinone衍生物，并在体外评估了其抑制醛糖还原酶（ALR2）的能力，醛糖还原酶是一种涉及糖尿病并发症出现的酶。化合物2e和2j具有显着的抑制作用，IC（50）分别为7.6和18 microM。这些化合物掺入了有效的药效基团，用于醛糖还原酶抑制活性，其特征是噻吩并nnolinone模板通过五亚甲基间隔基连接到羧基上。