5-methylene-7-(benzyloxycarbonylamino)-5,7,8,9-tetrahydrobenzocyclohepten-6-one | 1023620-57-6

• 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: 5-methylene-7-(benzyloxycarbonylamino)-5,7,8,9-tetrahydrobenzocyclohepten-6-one
• 英文别名: 5-methylene-7-(benzyloxycarbonyl-amino)-5,7,8,9-tetrahydro-benzocyclohepten-6-one；benzyl N-(5-methylidene-6-oxo-8,9-dihydro-7H-benzo[7]annulen-7-yl)carbamate
• CAS: 1023620-57-6
• 化学式: C₂₀H₁₉NO₃
• 分子量: 321.376
• InChiKey: LMVRUFHIZUMNCU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-methylene-7-(benzyloxycarbonylamino)-5,7,8,9-tetrahydrobenzocyclohepten-6-one 在 盐酸 、 copper(I) bromide dimethylsulfide complex 、 5%-palladium/activated carbon 、 氢气 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醚 、 水 为溶剂， 反应 26.75h， 生成 cis-5-(2-phenylethyl)-7-amino-5,7,8,9-tetrahydrobenzocyclohepten-6-one hydrochloride
  参考文献：
  名称：

  Rapid and efficient synthesis of a novel series of substituted aminobenzosuberone derivatives as potent, selective, non-peptidic neutral aminopeptidase inhibitors

  摘要：

  Racemic 5-substituted 7-aminobenzocyclohepten-6-one were synthesized and evaluated for their ability to inhibit metalloaminopeptidase activities. Unexpectedly, 5-thio substituted compounds showed enhanced inhibition potency with K-i values in the nanomolar range against the 'one zinc' aminopeptidases from the M1 family, while most of them were rather poor inhibitors of the 'two zincs' enzymes from the M17 family. This interesting selectivity profile may guide the design of new, specific inhibitors of target mammalian aminopeptidases with one active site zinc. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.06.041
• 作为产物：
  描述：

  聚合甲醛 、 7-(benzyloxycarbonylamino)-6,7,8,9-tetrahydro-benzocyclohepten-6-one 在 四氢吡咯 作用下， 以 溶剂黄146 为溶剂， 反应 5.0h， 生成 5-methylene-7-(benzyloxycarbonylamino)-5,7,8,9-tetrahydrobenzocyclohepten-6-one
  参考文献：
  名称：

  AMINOBENZOCYCLOHEPTENE DERIVATIVES, METHODS FOR PREPARING THE SAME AND USES THEREOF IN THERAPY

  摘要：

  一种具有一般化学式（I）的化合物作为治疗癌症的活性成分，特别是肿瘤，特别是涉及金属蛋白酶抑制的疾病，如氨基肽酶-N。包括具有一般化学式（I）的化合物的药物组合物。使用一般化学式（I）的化合物进行治疗的方法。

  公开号：

  US20100069504A1

文献信息

• AMINOBENZOCYCLOHEPTENE DERIVATIVES, METHODS FOR PREPARING THE SAME AND USES THEREOF IN THERAPY
  申请人：Tarnus-Rondeau Céline

  公开号：US20100069504A1

  公开（公告）日：2010-03-18

  A compound of the general formula (I) as an active principle for treating cancer, specifically tumors, in particular diseases involving inhibition of metalloproteases, such as Aminopeptidase-N. Pharmaceutical compositions comprising the compound of general formula (I). Methods of treatment using the compound of general formula (I).

  一种具有一般化学式（I）的化合物作为治疗癌症的活性成分，特别是肿瘤，特别是涉及金属蛋白酶抑制的疾病，如氨基肽酶-N。包括具有一般化学式（I）的化合物的药物组合物。使用一般化学式（I）的化合物进行治疗的方法。
• DERIVES D'AMINOBENZOCYCLOHEPTENE, LEURS PROCEDES DE PREPARATION ET LEUR UTILISATION EN THERAPEUTIQUE
  申请人：Universite De Haute Alsace

  公开号：EP2084125A1

  公开（公告）日：2009-08-05
• [EN] AMINOBENZOCYCLOHEPTENE DERIVATIVES, METHODS FOR PREPARING THE SAME AND USES THEREOF IN THERAPY<br/>[FR] DERIVES D' AMINOBENZOCYCLOHEPTENE, LEURS PROCEDES DE PREPARATION ET LEUR UTILISATION EN THERAPEUTIQUE
  申请人：UNIV HAUTE ALSACE

  公开号：WO2008059141A1

  公开（公告）日：2008-05-22

  [EN] The invention relates to a compound of the general formula (I) : F(I) in which: R₁, R₂, R₃, R₄, R₅, R₆, R₉, R₁₀, R₁₁ further represent a (C₁-C₆) alkoxy, (C₁-C₆) aralkyloxy, (C₁-C₆) alkylthio, (Q₁- C₆) aralkylthio radical; R₉ et R₁₁ can also form together a carbonated cycle or heterocycle or can form a double bond with the two carbon atoms adjacent to the heptene cycle; R₁ et R₂ can form together a carbonated cycle or heterocycle; or R₁ can be bonded to the heptene cycle by a double bond while R₂ is absent; R₃, R₄, R₅ and R₆ further represent a polyfluoro (C₁-C₆) alkyl, (C₁-C₆) alkoxy radical, an aryl or heteroaryl group; R₃ and R₄, R₄ and R₅, R₅ and R₆ can further form together a methylenedioxy radical joining the adjacent carbon atoms or an aromatic carbonated cycle or an aromatic heterocycle; R₇ is a hydrogen atom, a (C₁-C₆) alkyl radical; X is an oxygen or sulphur atom, N-R₁₂, N-O-R₁₃, in which R₁₂ and R₁₃ represent a hydrogen atom, a (C₁-C₆) alkyl, (C₁- C₆) (cycloalkyl) alkyl, (C₁-C₆) (heterocycloalkyl) alkyl, (C₁-C₆) aralkyl, (Ci-C6) heteroaralkyl radical; Y is a carbon atom; a nitrogen atom R₈ or R₉ being then absent; the invention also relates to addition salts with acids except the compound for which R₄, R₅, R₆ represent a methoxy radical, R₁, R₂, R₃, R₇ to R₁₁ represent a hydrogen atom, X represents an oxygen atom and Y represents a carbon atom.
  [FR] Composé répondant à la formule générale (I): F(I) dans laquelle R₁, R₂, R₃, R₄, R₅, R₆, R₉, R₁₀, R₁₁ représentent en outre un radical (C₁-C₆) alcoxy, (C₁-C₆) aralkyloxy, (C₁-C₆) al kylthio, (Q₁- C₆) aralkylthio; R₉ et R₁₁
• Rapid and efficient synthesis of a novel series of substituted aminobenzosuberone derivatives as potent, selective, non-peptidic neutral aminopeptidase inhibitors
  作者：Sébastien Albrecht、Emmanuel Salomon、Albert Defoin、Céline Tarnus

  DOI：10.1016/j.bmc.2012.06.041

  日期：2012.8

  Racemic 5-substituted 7-aminobenzocyclohepten-6-one were synthesized and evaluated for their ability to inhibit metalloaminopeptidase activities. Unexpectedly, 5-thio substituted compounds showed enhanced inhibition potency with K-i values in the nanomolar range against the 'one zinc' aminopeptidases from the M1 family, while most of them were rather poor inhibitors of the 'two zincs' enzymes from the M17 family. This interesting selectivity profile may guide the design of new, specific inhibitors of target mammalian aminopeptidases with one active site zinc. (C) 2012 Elsevier Ltd. All rights reserved.