3-Benzocyclobutyl-propionsaeure | 92545-69-2

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 3-Benzocyclobutyl-propionsaeure
• 英文别名: 3-(benzocyclobutan-1-yl)propionic acid；3-(7-bicyclo[4.2.0]octa-1,3,5-trienyl)propanoic acid
• CAS: 92545-69-2
• 化学式: C₁₁H₁₂O₂
• 分子量: 176.215
• InChiKey: QFZKEOSMVCUZSD-UHFFFAOYSA-N

物化性质

• 沸点：
  345.3±11.0 °C(Predicted)
• 密度：
  1.178±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-Benzocyclobutyl-propionsaeure 在 lithium aluminium tetrahydride 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 1-[3-(7-bicyclo[4.2.0]octa-1,3,5-trienyl)propyl]-4-(3,4-dihydro-2H-1,5-benzodioxepin-6-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

文献信息

• Piperazine, piperidine and 1,2,5,6-tetrahydropyridine
  申请人：Adir et Compagnie

  公开号：US05684020A1

  公开（公告）日：1997-11-04

  A compound selected from those of formula: ##STR1## wherein: A-B, n, D and E are as defined in the specification, their racemic mixtures, and their optical isomers, and also the physiologically tolerable salts thereof with appropriate acids. The products of the invention may be used therapeutically.

  从以下式中选择的化合物：##STR1## 其中：A-B，n，D和E如规范中定义，它们的外消旋混合物，以及它们的光学异构体，以及与适当酸的生理耐受盐。本发明的产品可用于治疗。
• Chemistry of bivalent carbon intermediates—IV
  作者：C.D. Gutsche、G.L. Bachman、R.S. Coffey

  DOI：10.1016/s0040-4020(01)92713-9

  日期：1962.1

  By means of competition experiments phenylcarbene, generated from phenyldiazomethane, has been shown to be approximately equally reactive to the benzene ring (to form phenylcycloheptatriene) and to aliphatic CH2 bonds, to be approximately six times more reactive to aliphatic CH2 bonds than to aliphatic CH2 bonds, and to be very unreactive toward aromatic CH bonds. These data have been used as aids

  通过竞争实验苯基碳烯，从phenyldiazomethane生成的手段，已经被证明是近似相等反应性的苯环（以形成phenylcycloheptatriene）和脂族CH 2个键的，为大约六倍以上反应性脂族CH 2个键比脂族CH 2键，并且对芳族CH键非常不活泼。这些数据已被用来帮助解释两个先前报道的结果1 b，1 c分子内对应物；它们还用于解释2-正丁基苯基重氮甲烷的分解，该分解生成比例大约为6：5：1的三种环状产物2-乙基茚满，2-甲基四氢萘和苯并双氢呋喃，以及第四种烃产物1- （邻甲苯基）-丁烯-2，代表卡宾反应的新模式。研究了温度和光源对2-正丁基苯基重氮甲烷分解产物比例的影响。
• New amidino derivatives and their use as thrombin inhibitors
  申请人：Inghardt Tord

  公开号：US20070249578A1

  公开（公告）日：2007-10-25

  There is provided compounds of formula I wherein R 1 , R x , Y, R y , n and B have meanings given in the description which are useful as competitive inhibitors of trypsin-like proteases, such as thrombin, and in particular in the treatment of conditions where inhibition of thrombin is required (e.g. thrombosis) or as anticoagulants.

  提供了式I的化合物，其中R1、Rx、Y、Ry、n和B的含义如描述中所述，这些化合物可用作竞争性蛋白酶抑制剂，例如凝血酶，特别适用于需要抑制凝血酶的状况的治疗（例如血栓形成）或作为抗凝剂。
• US5194437A
  申请人：——

  公开号：US5194437A

  公开（公告）日：1993-03-16
• US5684020A
  申请人：——

  公开号：US5684020A

  公开（公告）日：1997-11-04