methyl 2-(7-oxo-4,5,6,7-tetrahydrobenzo[b]thiophen-6-yl)acetate | 114685-96-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-(7-oxo-4,5,6,7-tetrahydrobenzo[b]thiophen-6-yl)acetate
• 英文别名: 4,5,6,7-tetrahydro-7-keto-6-methoxycarbonylmethylthianaphthene；methyl 2-(7-oxo-5,6-dihydro-4H-1-benzothiophen-6-yl)acetate
• CAS: 114685-96-0
• 化学式: C₁₁H₁₂O₃S
• 分子量: 224.28
• InChiKey: GOLCVIPWAZUASL-UHFFFAOYSA-N

物化性质

• 沸点：
  340.4±22.0 °C(Predicted)
• 密度：
  1.247±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  71.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2-(7-oxo-4,5,6,7-tetrahydrobenzo[b]thiophen-6-yl)acetate 在 硫酸 、 铁粉 、 potassium nitrate 作用下， 以 溶剂黄146 为溶剂， 反应 9.0h， 生成 methyl 2-[3-(acetylamino)-7-oxo-4,5,6,7-tetrahydrobenzo[b]thiophen-6-yl]acetate
  参考文献：
  名称：

  Preparation of Thieno[3,2-h]cinnolinones as Matrix Metalloproteinase Inhibitors

  摘要：

  A new series of thieno[3,2-h]cinnolinone analogues was synthesized which is structurally related to 2,3,4,4a,5,6-hexahydro thieno[3,2-h]cinnolin-3-one 1, a weak inhibitor of the matrix metalloproteinase MMP-8 (human neutrophil collagenase). Preliminary SAR studies have shown that while C-4a-methyl, C-7-acetylamino, C-7 and C-8-nitro substitution, and C-4-C-4a olefination provided no increase in activity relative to 1, Cs-acetylamino substitution as in 5 and 8 was favourable. Moreover, to predict how the thieno[3,3-h]cinnolinone inhibitors might bind to MMP-8, the unsubstituted compound 9 was docked into the MMP-8 crystal structure. These studies revealed that inhibitor 9 does not seem to be able to coordinate the catalytically-active zinc ion but preferably interact with the peptide-binding region of the active site.

  DOI：

  10.1002/(sici)1521-4184(200002)333:2/3<37::aid-ardp37>3.0.co;2-v
• 作为产物：
  描述：

  5,6-二氢-1-苯并噻吩-7(4H)-酮 在 盐酸 作用下， 以 甲醇 、 乙醚 、 水 、 二甲基亚砜 、 丙酮 为溶剂， 反应 8.0h， 生成 methyl 2-(7-oxo-4,5,6,7-tetrahydrobenzo[b]thiophen-6-yl)acetate
  参考文献：
  名称：

  Preparation of Thieno[3,2-h]cinnolinones as Matrix Metalloproteinase Inhibitors

  摘要：

  A new series of thieno[3,2-h]cinnolinone analogues was synthesized which is structurally related to 2,3,4,4a,5,6-hexahydro thieno[3,2-h]cinnolin-3-one 1, a weak inhibitor of the matrix metalloproteinase MMP-8 (human neutrophil collagenase). Preliminary SAR studies have shown that while C-4a-methyl, C-7-acetylamino, C-7 and C-8-nitro substitution, and C-4-C-4a olefination provided no increase in activity relative to 1, Cs-acetylamino substitution as in 5 and 8 was favourable. Moreover, to predict how the thieno[3,3-h]cinnolinone inhibitors might bind to MMP-8, the unsubstituted compound 9 was docked into the MMP-8 crystal structure. These studies revealed that inhibitor 9 does not seem to be able to coordinate the catalytically-active zinc ion but preferably interact with the peptide-binding region of the active site.

  DOI：

  10.1002/(sici)1521-4184(200002)333:2/3<37::aid-ardp37>3.0.co;2-v

文献信息

• Thianaphthene derivatives
  申请人：Sankyo Company Limited

  公开号：US04847272A1

  公开（公告）日：1989-07-11

  Compounds of formula (I): ##STR1## (wherein n is 0 or 1, R.sup.1 and R.sup.2 are hydrogen or alkyl, one of A.sup.1 and A.sup.2 is --Z--Y and the other is --W--COOH, where W and Z are alkenylene or alkylene and Y is imidazolyl or pyridyl, and the broken lines represent two single bonds or one single bond and one double bond) and their salts, esters and amides have the ability to inhibit the synthesis of thromboxane A.sub.2 and hence are useful in the treatment or prophylaxis of thrombotic conditions. They may be prepared by introducing an imidazolyl or pyridyl group into the corresponding compound in which Y is replaced by an active group or atom.

  化合物的化学式（I）：##STR1##（其中n为0或1，R.sup.1和R.sup.2为氢或烷基，A.sup.1和A.sup.2中的一个为--Z--Y，另一个为--W--COOH，其中W和Z为烯烃基或烷基，Y为咪唑基或吡啶基，虚线代表两个单键或一个单键和一个双键），以及它们的盐、酯和酰胺具有抑制血栓素A.sub.2合成的能力，因此在治疗或预防血栓性疾病方面是有用的。它们可以通过将咪唑基或吡啶基引入相应的化合物中来制备，其中Y被活性基团或原子所取代。
• Thianaphthene derivatives, their production and use
  申请人：Sankyo Company Limited

  公开号：EP0240107B1

  公开（公告）日：1991-08-21
• US4847272A
  申请人：——

  公开号：US4847272A

  公开（公告）日：1989-07-11
• US5021444A
  申请人：——

  公开号：US5021444A

  公开（公告）日：1991-06-04
• Preparation of Thieno[3,2-h]cinnolinones as Matrix Metalloproteinase Inhibitors
  作者：Gérard A. Pinna、Maria M. Curzu、Gabriele Murineddu、Giorgio Chelucci、Giorgio Cignarella、Ernesto Menta、Hans W. Krell、Giulio Rastelli、Anna M. Ferrari

  DOI：10.1002/(sici)1521-4184(200002)333:2/3<37::aid-ardp37>3.0.co;2-v

  日期：2000.2

  A new series of thieno[3,2-h]cinnolinone analogues was synthesized which is structurally related to 2,3,4,4a,5,6-hexahydro thieno[3,2-h]cinnolin-3-one 1, a weak inhibitor of the matrix metalloproteinase MMP-8 (human neutrophil collagenase). Preliminary SAR studies have shown that while C-4a-methyl, C-7-acetylamino, C-7 and C-8-nitro substitution, and C-4-C-4a olefination provided no increase in activity relative to 1, Cs-acetylamino substitution as in 5 and 8 was favourable. Moreover, to predict how the thieno[3,3-h]cinnolinone inhibitors might bind to MMP-8, the unsubstituted compound 9 was docked into the MMP-8 crystal structure. These studies revealed that inhibitor 9 does not seem to be able to coordinate the catalytically-active zinc ion but preferably interact with the peptide-binding region of the active site.