(benzocyclobutan-1-yl)-methyl iodide | 135634-19-4

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: (benzocyclobutan-1-yl)-methyl iodide
• 英文别名: 7-(Iodomethyl)bicyclo[4.2.0]octa-1,3,5-triene
• CAS: 135634-19-4
• 化学式: C₉H₉I
• 分子量: 244.075
• InChiKey: MGIXHHGPONMWMN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-(2,3-二氢-1,4-苯并二烷-5-基)哌嗪盐酸盐 、 (benzocyclobutan-1-yl)-methyl iodide 在 sodium carbonate 作用下， 以 various solvent(s) 为溶剂， 反应 24.0h， 以30%的产率得到1-Bicyclo[4.2.0]octa-1(6),2,4-trien-7-ylmethyl-4-(2,3-dihydro-benzo[1,4]dioxin-5-yl)-piperazine
  参考文献：
  名称：

  Characterization of Potent and Selective Antagonists at Postsynaptic 5-HT1A Receptors in a Series of N4-Substituted Arylpiperazines

  摘要：

  Benzocycloalkyl and benzocycloalkenyl moities linked, directly or via an alkyl chain, to oxygen-bearing heteroarylpiperazines were synthesized, in an attempt to obtain potent and selective antagonists at postsynaptic 5-HT1A receptors. From the numerous arylpiperazines described in the literature, 1-(2,3-dihydro-1,4-benzodioxin-5-yl)pipe (3a) was chosen as a model of an arylpiperazine in view of its selectivity for 5-HT1A receptors versus alpha(1)-, alpha(2)-, and beta-adrenergic receptors, as well as dopamine D-1 and D-2 receptors. Two other closely-related arylpiperazines, 1-(1,5-benzodioxepin-6-yl)piperazine (3b) and 1-(benzofuran-7-yl)piperazine (3c), were also examined in this study. Al compounds showed high affinity at 5-HT1A sites (8.10 less than or equal to pK(i)s less than or equal to 9.35), and the majority behaved as antagonists in vivo in blocking the hypothermia induced by the 5-HT1A agonist 8-OH-DPAT in the absence of a marked effect alone at equivalent doses. An in vivo evaluation of dopamine D-2 receptor antagonist properties revealed that the majority of compounds was devoid of activity at this site, in marked contrast to BMY 7378 which displayed virtually no selectivity for 5-HT1A versus dopamine D-2 receptors. Moreover, six compounds of the present series, 8, 10, 11, 14, 25, and, 37, showed > 10-fold selectivity in vitro for 5-HT1A versus alpha(1)-adrenergic receptors. Compound 14 displayed an optimal compromise between potency (pK(i) = 8.75), marked antagonist activity, and selectivity toward alpha(1)-adrenergic (81-fold) and dopamine D-2 (195-fold) receptors. These characteristics clearly distinguish 14 from previously-reported ligands such as the postsynaptic 5-HT1A antagonist BMY 7378 and the weak partial agonist NAN 190 which, in contrast to the compounds of this series, belong to the well-exemplified class of imido derivatives of (o-methoxyphenyl)piperazines. The availability of 14 (S 15535) should facilitate the further elucidation of the functional role and potential therapeutic significance of 5-HT1A receptors.

  DOI：

  10.1021/jm00020a020
• 作为产物：
  描述：

  bicyclo[4.2.0]octa-1,3,5-trien-7-ylmethyl 4-methylbenzenesulfonate 在 sodium iodide 作用下， 以 水 、 丙酮 为溶剂， 以88%的产率得到(benzocyclobutan-1-yl)-methyl iodide
  参考文献：
  名称：

  Benzisoxazole and benzisothiazole compounds

  摘要：

  这些化合物是N-取代的N'-(苯并异噁唑基或苯并异硫唑基)哌嗪，可用作镇静剂、抗焦虑剂、抗攻击剂和镇痛剂，用于治疗精神分裂症和抑郁症。其中一种化合物是(R,S)-3-{1-[(苯并环丁基)甲基]哌嗪-4-基}-6-氟-1,2-苯并异噁唑。

  公开号：

  US05173490A1

文献信息

• Aminopiperidine indanyl and benzocyclobutene compounds
  申请人：Adir et Compagnie

  公开号：US05189045A1

  公开（公告）日：1993-02-23

  The invention relates to new compounds of formula I: ##STR1## in which: m represents zero, 1, 2, 3 or 4, n and p represent zero, 1 or 2, W represents an oxygen atom, an --NH-- radical, or a single bond, R represents a benzocyclobuten-1-yl radical, or an indanyl radical, a 2,3-dihydrobenzofuran-2-yl R.sub.1 represents a hydrogen atom, an alkyl radical having from 1 to 6 carbon atoms, or an aryl radical, and R.sub.2 represents a hydrogen atom, an alkyl radical, an alkenyl radical, a cycloalkyl radical, a benzyl radical, a phenyl radical, an aralkyl radical, an alkoxyalkyl radical or a polyhalogenated alkyl radical, the optical isomers thereof and the addition salts thereof with a pharmaceutically acceptable organic or mineral acid, and medicaments containing the same.

  该发明涉及公式I的新化合物：##STR1## 其中：m表示零，1，2，3或4，n和p表示零，1或2，W表示氧原子，--NH--基团或单键，R表示苯并环丁-1-基基团或茚基基团，2,3-二氢苯并呋喃-2-基团，R.sub.1表示氢原子，具有1至6个碳原子的烷基基团或芳基基团，R.sub.2表示氢原子，烷基基团，烯基基团，环烷基基团，苯甲基基团，苯基基团，芳基烷基基团，烷氧基烷基基团或多卤代烷基基团，其光学异构体及其与药学上可接受的有机或无机酸的加成盐和含有它们的药物。
• Aminopiperidine 4-oxo-4H-chromen-2-yl compounds
  申请人：Adir et Compagnie

  公开号：US05214055A1

  公开（公告）日：1993-05-25

  The invention relates to new compounds of formula I: ##STR1## in which: m represents zero, 1, 2, 3 or 4, n and p represent zero, 1 or 2, W represents an oxygen atom, an --NH-- radical, or a single bond, R represents a 4-oxo-4H-chromen-2-yl radical, R.sub.1 represents a hydrogen atom, an alkyl radical having from 1 to 6 carbon atoms, or an aryl radical, and R.sub.2 represents a hydrogen atom, an alkyl radical, an alkenyl radical, a cycloalkyl radical, a benzyl radical, a phenyl radical, an aralkyl radical, an alkoxyalkyl radical or a polyhalogenated alkyl radical, the optical isomers thereof and the addition salts thereof with a pharmaceutically acceptable organic or mineral acid, and medicaments containing the same, are disclosed.

  本发明涉及式I的新化合物：##STR1## 其中：m表示零，1，2，3或4，n和p表示零，1或2，W表示氧原子，--NH--基团或单键，R表示4-氧代-4H-香豆素-2-基基团，R.sub.1表示氢原子，具有1至6个碳原子的烷基基团或芳基基团，R.sub.2表示氢原子，烷基基团，烯基基团，环烷基基团，苄基基团，苯基基团，芳基烷基基团，烷氧基烷基基团或多卤代烷基基团，其光学异构体以及与药学上可接受的有机或无机酸的加合物，以及包含它们的药物。
• 1,2-benzisoxazole compounds
  申请人：Adir et Compagnie

  公开号：US05100902A1

  公开（公告）日：1992-03-31

  Compounds of formula I ##STR1## in which m represents an integer from 0 to 5, n represents an integer from 1 to 2, p is equal to 0, 1 or 2, X, Y and Z, which may be identical or different, each represent a hydrogen atom, a halogen atom, a linear or branched alkyl radical, a trifluoromethyl radical, an alkoxy radical, an alkylthio radical or a hydroxyl radical, and R represents a 2-benzofuranyl or 2,3-dihydro-2-benzofuranyl radical (it being possible for each to be substituted on the benzene ring), a 2,3,6,7-tetrahydrobenzo[1,2-b:4,5-b']difuran-2-yl radical, a 4-oxo-4H-chromen-2-yl radical (optionally substituted on the benzene ring), a benzocyclobutenyl radical of formula A or an indanyl radical of formula B: ##STR2## (in which: R.sub.1 and R.sub.2, which may be identical or different, each represent a hydrogen atom, a halogen atom, a trifluoromethyl radical, an alkyl radical, an alkoxy radical, a hydroxyl radical, a hydroxyalkyl radical or an alkylthio radical, or together form a methylenedioxy radical or an ethylenedioxy radical, and R.sub.3 represents a hydrogen atom or a linear or branched alkyl radical having 1 to 6 carbon atoms), or a radical of formula C: ##STR3## (in which R.sub.4, R.sub.5 and R.sub.6, which may be identical or different, each represent a hydrogen atom, a halogen atom, a trifluoromethyl radical, a hydroxyl radical, an alkyl radical, an alkoxy radical or an alkylthio radical, their optical isomers and their addition salts with a pharmaceutically acceptable organic or inorganic acid.

  式I的化合物##STR1##，其中m表示0到5的整数，n表示1到2的整数，p等于0、1或2，X、Y和Z可以相同也可以不同，分别表示氢原子、卤素原子、线性或支链烷基、三氟甲基基、烷氧基、烷基硫基或羟基基团，而R表示2-苯并呋喃基或2,3-二氢-2-苯并呋喃基（每个基团都可能在苯环上取代）、4-氧代-4H-香豆素-2-基基团（在苯环上可选择性取代）、式A的苯环戊二烯基基团或式B的茚基基团：##STR2##（其中：R.sub.1和R.sub.2，可以相同也可以不同，分别表示氢原子、卤素原子、三氟甲基基团、烷基、烷氧基、羟基、羟基烷基或烷基硫基，或者一起形成甲二氧基基团或乙二氧基基团，而R.sub.3表示氢原子或具有1到6个碳原子的线性或支链烷基基团），或式C的基团：##STR3##（其中R.sub.4、R.sub.5和R.sub.6，可以相同也可以不同，分别表示氢原子、卤素原子、三氟甲基基团、羟基基团、烷基、烷氧基或烷基硫基团，它们的光学异构体和其与药学上可接受的有机或无机酸的加成盐）。
• US5173490A
  申请人：——

  公开号：US5173490A

  公开（公告）日：1992-12-22
• US5194437A
  申请人：——

  公开号：US5194437A

  公开（公告）日：1993-03-16