3-bromo-4,5,6,7-tetrahydro-benzo[b]thiophene-7-one | 274925-56-3

• 物质功能分类: 医药中间体 - 杂环化合物 - 噻吩类化合物
• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-bromo-4,5,6,7-tetrahydro-benzo[b]thiophene-7-one
• 英文别名: 3-Bromo-5,6-dihydrobenzo[b]thiophen-7(4H)-one；3-bromo-5,6-dihydro-4H-1-benzothiophen-7-one
• CAS: 274925-56-3
• 化学式: C₈H₇BrOS
• 分子量: 231.113
• InChiKey: WERAVPKEVZCHHA-UHFFFAOYSA-N

物化性质

• 沸点：
  331.4±42.0 °C(Predicted)
• 密度：
  1.669±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  45.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  3-bromo-4,5,6,7-tetrahydro-benzo[b]thiophene-7-one 在 sodium hydroxide 作用下， 以 甲醇 、 氯仿 、 水 、 二甲基亚砜 、 丙酮 为溶剂， 反应 9.5h， 生成 2-(3-bromo-7-oxo-4,5,6,7-tetrahydrobenzo[b]thiophen-6-yl)acetic acid
  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 溴 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 24.0h， 以76.8%的产率得到3-bromo-4,5,6,7-tetrahydro-benzo[b]thiophene-7-one
  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

• Pharmaceutical compounds wiht angiogenesis inbhibitory activity
  申请人：Kemotech S.r.l.

  公开号：EP2789619A1

  公开（公告）日：2014-10-15

  Compounds of formula (I): wherein: A, R, T, Q, L, Z, G, X and A' are as defined in the description. B and D, equal to or different from each other, are selected between heteroaryl and aryl, wherein at least one of the hydrogen atoms of said heteroaryl and aryl are substituted with groups selected from SO3-, SO3H, COO-, COOH, and one or more of the other hydrogen atoms of said heteroaryl and aryl are optionally substituted as reported in the description.

  式（I）的化合物：其中：A、R、T、Q、L、Z、G、X和A'如描述中所定义。B和D，相等或不同，选自杂芳基和芳基，其中所述杂芳基和芳基的至少一个氢原子被取代为SO3-、SO3H、COO-、COOH中的一种或几种基团，所述杂芳基和芳基的其他氢原子可选择性地被取代，如描述中所述。
• US2014/343294
  申请人：——

  公开号：——

  公开（公告）日：——
• US20140343294A1
  申请人：——

  公开号：US20140343294A1

  公开（公告）日：2014-11-20
• US9181196B2
  申请人：——

  公开号：US9181196B2

  公开（公告）日：2015-11-10
• 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.