4-acetyl-3,4,5,6-tetrahydro-2H-1,5-methano-1,4-benzodiazocine | 80770-20-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 4-acetyl-3,4,5,6-tetrahydro-2H-1,5-methano-1,4-benzodiazocine
• 英文别名: 4-Acetyl-3,4,5,6-Tetrahydro-2H-1,5-methano-benzo<1.4>diazocin；4-acetyl-3,4,5,6-tetrahydro-2H-1,5-methano-benzo[e][1,4]diazocine；1-(1,10-diazatricyclo[7.3.1.02,7]trideca-2,4,6-trien-10-yl)ethanone
• CAS: 80770-20-3
• 化学式: C₁₃H₁₆N₂O
• 分子量: 216.283
• InChiKey: MZWCDEZZDNORPQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-acetyl-3,4,5,6-tetrahydro-2H-1,5-methano-1,4-benzodiazocine 在 盐酸 、 硫酸 、 potassium nitrate 作用下， 反应 4.0h， 生成 3,4,5,6-tetrahydro-9-nitro-2H-1,5-methano-1,4-benzodiazocine dihydrochloride
  参考文献：
  名称：

  Synthesis and antinociceptive activity of 4-(cyclopropylmethyl)-3,4,5,6-tetrahydro-2H-1,5-methano-1,4-benzodiazocin-9-amine and congeners

  摘要：

  The synthesis of 1,4-benzodiazocines has been extended to include the 9-amines. The title compound, 6, was prepared from the known nor-base by N-acylation with cyclopropanecarboxylic acid anhydride, followed by nitration of the aromatic ring and sequential reduction of the resulting nitroamide. Standard in vivo bioassays for antinociceptive and opiate antagonist activities indicated that 6 is an analgesic agonist mixed narcotic antagonist whose oral to parenteral activity ratio approaches unity. Resolution of 6 established that the activity of the racemate resides in the dextrorotatory antipode. Several congeners were also prepared and tested. Their synthesis and structure-activity relationships are given in this paper.

  DOI：

  10.1021/jm00383a007
• 作为产物：
  描述：

  (-)-3,4,5,6-tetrahydro-2H-1,5-methano-1,4-benzodiazocine 、 乙酸酐 以94%的产率得到
  参考文献：
  名称：

  GUBITZ, F. W., J. MED. CHEM., 1985, 28, N 6, 728-733

  摘要：

  DOI：

文献信息

• Alicyclic carboxylic acid derivatives of benzomorphans and related scaffolds, medicaments containing such compounds and their use
  申请人：Peters Stefan

  公开号：US20110269791A1

  公开（公告）日：2011-11-03

  The present invention relates to compounds defined by Formula (I), wherein the groups A, B, X, m, n and o are defined as in claim 1, possessing valuable pharmacological activity. Particularly the compounds are inhibitors of 11β-hydroxysteroid dehydrogenase (HSD) 1 and thus are suitable for treatment and prevention of diseases which can be influenced by inhibition of this enzyme, such as metabolic diseases, in particular diabetes type 2, obesity and dyslipidemia.

  本发明涉及由式（I）定义的化合物，其中A、B、X、m、n和o基团的定义如权利要求1中所述，具有有价值的药理活性。特别是这些化合物是11β-羟基类固醇脱氢酶（HSD）1的抑制剂，因此适用于治疗和预防可以受到该酶抑制影响的疾病，如代谢性疾病，特别是2型糖尿病、肥胖症和血脂异常。
• 1,5-Methano-1,4-benzodiazocines, intermediates therefor, and method of
  申请人：Sterling Drug Inc.

  公开号：US04299830A1

  公开（公告）日：1981-11-10

  4-Q-9-RR'N-3,4,5,6-tetrahydro-2H-1,5-methano-1,4-benzodiazocines wherein Q is propyl, isobutyl, neopentyl, allyl, 2-methyl-2-propenyl, 2-chloro-2-propenyl, cis-3-chloro-2-propenyl, cis-3-chloro-2-butenyl, trans-3-chloro-2-butenyl, propargyl, cyclopropylmethyl or (2,2-dichlorocyclopropyl)methyl; and R and R' are both hydrogens or both methyls; or R is hydrogen and R' is methyl, ethyl, propyl, butyl, isobutyl or benzyl and acid addition salts thereof are useful as strong analgesics and are prepared from the known 3,4,5,6-tetrahydro-2H-1,5-methano-1,4-benzodiazocine by multi-step processes including acylation (including acetylation), nitration, nitro reduction, amide reduction, deacetylation, alkylation and dimethylation.

  4-Q-9-RR'N-3,4,5,6-四氢-2H-1,5-甲基-1,4-苯并二氮杂环，其中Q为丙基，异丁基，新戊基，烯丙基，2-甲基-2-丙烯基，2-氯-2-丙烯基，顺-3-氯-2-丙烯基，顺-3-氯-2-丁烯基，反-3-氯-2-丁烯基，丙炔基，环丙基甲基或(2,2-二氯环丙基)甲基；R和R'均为氢或甲基；或R为氢，而R'为甲基，乙基，丙基，丁基，异丁基或苄基，其酸盐可用作强镇痛剂，并通过多步反应制备自已知的3,4,5,6-四氢-2H-1,5-甲基-1,4-苯并二氮杂环，包括酰化（包括乙酰化），硝化，硝基还原，酰胺还原，去乙酰化，烷基化和二甲基化。
• US4299830A
  申请人：——

  公开号：US4299830A

  公开（公告）日：1981-11-10
• US8765780B2
  申请人：——

  公开号：US8765780B2

  公开（公告）日：2014-07-01
• US9073870B2
  申请人：——

  公开号：US9073870B2

  公开（公告）日：2015-07-07