4-(3,4-二氯苯基)-1,2,3,6-四氢吡啶 | 153655-92-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-(3,4-二氯苯基)-1,2,3,6-四氢吡啶
• 英文名称: 4-(3,4-dichlorophenyl)-1,2,3,6-tetrahydropyridine
• 英文别名: 4-(3,4-dichlorophenyl)-3,6-dihydro-2H-pyridine
• CAS: 153655-92-6
• 化学式: C₁₁H₁₁Cl₂N
• mdl: MFCD11128345
• 分子量: 228.121
• InChiKey: OENHQMQUZYKXFG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-(3,4-二氯苯基)-1,2,3,6-四氢吡啶 在 盐酸 、 sodium hydride 、 二异丙胺 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 乙二醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 生成
  参考文献：
  名称：

  设计，合成和结构亲和关系的4-亚甲基哌啶和4-芳基-1,2,3,6-四氢吡啶衍生物作为促肾上腺皮质激素释放因子1受体拮抗剂。

  摘要：

  最近，已经报道了各种非肽促肾上腺皮质激素释放因子1（CRF1）受体拮抗剂。非肽CRF拮抗剂的结构亲和关系（SAR）表明，此类拮抗剂可以由三个单元构成：疏水单元（上区域），质子接受单元（中区域）和芳族单元（下区域）区）。我们的兴趣集中在向上区域上，以衍生出作为非肽CRF1受体拮抗剂的新型亚甲基亚哌啶衍生物8-10和4-芳基-1,2,3,6-四氢吡啶衍生物11-13。化合物8a和11a对CRF1受体具有中等亲和力，但化合物9、10、12和13不显示CRF1受体亲和力。衍生物11的修饰得到化合物11i（CRA1001）和11x（CRA1000），在某些实验动物模型中，其对CRF1受体具有高亲和力和选择性，并具有有效的抗焦虑药样和抗抑郁药样特性。这些发现表明，疏水单元（Up-Area）可能对设计CRF1拮抗剂有用。我们在这里报告衍生物8和11以及等位基因9、10、12和13的设计，合成和SAR。

  DOI：

  10.1016/s0968-0896(00)00045-6
• 作为产物：
  描述：

  3,4-二氯溴苯 在 potassium phosphate 、 四(三苯基膦)钯 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 反应 23.0h， 生成 4-(3,4-二氯苯基)-1,2,3,6-四氢吡啶
  参考文献：
  名称：

  Synthesis and biological evaluation of 1-(isoxazol-5-ylmethylaminoethyl)-4-phenyl tetrahydropyridine and piperidine derivatives as potent T-type calcium channel blockers with antinociceptive effect in a neuropathic pain model

  摘要：

  New tetrahydropyridinyl and piperidinyl ethylamine derivatives were designed with hypothetical mapping on pharmacophore model generated from ligand-based virtual screening. The designed compounds were synthesized, and their inhibitory activities on T-type calcium channel were assayed using FDSS and patch-clamp assay. Among them, compounds 7b and 10b showed potent T-type calcium current blocking activity against Ca(v)3.1 (alpha(1G)) and Ca(v)3.2 (alpha(1H)) channel simultaneously. With hERG and pharmacokinetics studies, compounds 7b and 10b were evaluated for the antinociceptive effect on rat model of neuropathic pain. They were significantly effective in decreasing the pain responses to mechanical and cold allodynia induced by spinal nerve ligation. These results suggest that modulation of alpha(1G) and am subtype T-type calcium channels may provide a promising approach for the treatment of neuropathic pain. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.12.056

文献信息

• Phenoxypropylamine compounds
  申请人：——

  公开号：US20020111358A1

  公开（公告）日：2002-08-15

  The present invention relates to a phenoxypropylamine compound of the formula (I) 1 wherein each symbol is as defined in the specification, an optically active compound thereof or a pharmaceutically acceptable salt thereof and hydrates thereof, which simultaneously show selective affinity for and antagonistic activity against 5-HT 1A receptor, as well as 5-HT reuptake inhibitory activity, and can be used as antidepressants quick in expressing an anti-depressive effect.

  本发明涉及一种公式（I）中的苯氧丙胺化合物： 1 其中每个符号如说明书中所定义，其光学活性化合物或其药物可接受的盐及水合物，同时显示出对5-HT 1A 受体的选择性亲和力和拮抗活性，以及5-HT再摄取抑制活性，并且可以用作快速表达抗抑郁效果的抗抑郁药。
• 4-Tetrahydropyridylpyrimidine derivatives
  申请人：Taisho Pharmaceutical Co., Ltd.

  公开号：US06187781B1

  公开（公告）日：2001-02-13

  A 4-tetrahydropyridylpyrimidine compound represented by formula (I): wherein Ar represents a phenyl group substituted with 1 to 3 substituents selected from a halogen atom, an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, and a trifluoromethyl group, a phenyl group, a thienyl group or a furanyl group; R1 represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, an amino group or an amino group substituted with 1 or 2 alkyl groups having 1 to 5 carbon atoms; R2 represents an alkyl group having 1 to 5 carbon atoms, a cycloalkylalkyl group having 4 to 7 carbon atoms, an alkenyl group having 2 to 5 carbon atoms or an alkynyl group having 2 to 5 carbon atoms; and X1, X2, and X3, which may be the same or different, each represent a hydrogen atom, a halogen atom, an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an alkylthio group having 1 to 5 carbon atoms, an amino group or an amino group substituted with 1 or 2 alkyl groups having 1 to 5 carbon atoms, or a pharmaceutically acceptable salt thereof. The 4-Tetrahydropyridylpyrimidine compound finds utility in the treatment of diseases in which CRF is implicated.

  公式（I）所代表的一种4-四氢吡啶基嘧啶化合物： 其中Ar代表一个苯基，该苯基被1至3个取自卤素原子、具有1至5个碳原子的烷基、具有1至5个碳原子的烷氧基和三氟甲基、苯基、噻吩基或呋喃基的取代基所取代；R1代表氢原子、具有1至5个碳原子的烷基、氨基或被1或2个具有1至5个碳原子的烷基取代的氨基；R2代表具有1至5个碳原子的烷基、具有4至7个碳原子的环烷基烷基、具有2至5个碳原子的烯基或具有2至5个碳原子的炔基；X1、X2和X3，可以相同也可以不同，每个代表氢原子、卤素原子、具有1至5个碳原子的烷基、具有1至5个碳原子的烷氧基、具有1至5个碳原子的烷硫基、氨基或被1或2个具有1至5个碳原子的烷基取代的氨基，或其药学上可接受的盐。这种4-四氢吡啶基嘧啶化合物在治疗涉及CRF的疾病中具有用途。
• Indoline derivatives
  申请人：H. Lundbeck A/S

  公开号：US20040044007A1

  公开（公告）日：2004-03-04

  The present invention relates to methods of treating psychiatric or neurologic disorders, in particular psychoses, by administration of a compound formula of (I) 1 wherein R 1 is acyl, thioacyl, trifluoromethylsulfonyl or R 1 is a group R 12 SO 2 —, R 12 OCO— or R 12 SCO— wherein R 12 is C 1-6 -alkyl, C 2-6 -alkenyl, C 2-6 -alkynyl, C 3-8 -cycloalkyl, C 3-8 -cycloalkyl-C 1-6 -alkyl or aryl, or R 1 is a group R 13 R 14 NCO, R 13 R 14 NCS—, wherein R 13 and R 14 are independently hydrogen, C 1-6 -alkyl, C 2-6 -alkenyl, C 2-6 -alkynyl, C 3-8 -cycloalkyl, C 3-8 -cycloalkyl-C 1-6 -alkyl or aryl, or R 13 and R 14 together with the N-atom to which they are linked form a pyrrolidinyl, piperidinyl or perhydroazepin group; n is 1-6; X is C, CH or N, and the dotted line emanating from X indicates a bond when X is C and no bond when X is N or CH; R′, R″ and R 2 are independently selected from hydrogen and C 1-6 -alkyl; R 3 -R 11 are independently selected from hydrogen, halogen, cyano, nitro, C 1-6 -alkyl, C 2-6 -alkenyl, C 2-6 -alkynyl, C 3-8 -cycloalkyl, C 3-8 -cycloalkyl-C 1-6 -alkyl, amino, C 1-6 -alkylamino, di-(C 1-6 -alkyl)amino, C 1-6 -alkylcarbonyl, aminocarbonyl, C 1-6 -alkylaminocarbonyl, di-(C 1-6 -alkyl)aminocarbonyl, C 1-6 -alkoxy, C 1-6 -alkylthio, hydroxy, trifluoromethyl, trifluoromethylsulfonyl and C 1-6 -alkylsulfonyl; or a pharmaceutically acceptable acid addition salt thereof.

  本发明涉及通过给予(I)1式化合物的配方治疗精神或神经疾病，特别是精神病，其中R1为酰基，硫酰基，三氟甲基磺酰基，或R1为R12SO2—，R12OCO—或R12SCO—的基团，其中R12为C1-6烷基，C2-6烯基，C2-6炔基，C3-8环烷基，C3-8环烷基-C1-6烷基或芳基，或R1为R13R14NCO，R13R14NCS—的基团，其中R13和R14分别为氢，C1-6烷基，C2-6烯基，C2-6炔基，C3-8环烷基，C3-8环烷基-C1-6烷基或芳基，或R13和R14与它们连接的N原子一起形成吡咯烷基，哌啶基或过氢杂环庚烷基；n为1-6；X为C，CH或N，从X发出的点线表示当X为C时为一条键，当X为N或CH时为无键；R′，R″和R2独立选择自氢和C1-6烷基；R3-R11独立选择自氢，卤素，氰基，硝基，C1-6烷基，C2-6烯基，C2-6炔基，C3-8环烷基，C3-8环烷基-C1-6烷基，氨基，C1-6烷基氨基，二-(C1-6烷基)氨基，C1-6烷基羰基，氨基羰基，C1-6烷基氨基羰基，二-(C1-6烷基)氨基羰基，C1-6烷氧基，C1-6烷基硫基，羟基，三氟甲基，三氟甲基磺酰基和C1-6烷基磺酰基；或其药学上可接受的酸盐。
• PIPERIDINYL DERIVATIVES AS MODULATORS OF CHEMOKINE RECEPTOR ACTIVITY
  申请人：Carter Percy H.

  公开号：US20070208056A1

  公开（公告）日：2007-09-06

  The present application describes substituted piperidinyl modulators of MIP-1α or CCR-1 or stereoisomers or pharmaceutically acceptable salts thereof. In addition, methods of treating and preventing inflammatory diseases such as asthma and allergic diseases, as well as autoimmune pathologies such as rheumatoid arthritis and transplant rejection using said modulators are disclosed.

  本申请描述了MIP-1α或CCR-1的取代哌啶调节剂或其立体异构体或药学上可接受的盐。此外，还公开了使用上述调节剂治疗和预防炎症性疾病，如哮喘和过敏性疾病，以及自身免疫病理学，如类风湿性关节炎和移植排斥等方法。
• 2,3-Dihydro-6-nitroimidazo[2,1-b]oxazoles
  申请人：Tsubouchi Hidetsugu

  公开号：US20060094767A1

  公开（公告）日：2006-05-04

  The present invention provides a 2,3-dihydro-6-nitroimidazo[2,1-b]oxazole compound represented by the following general formula: wherein R 1 represents a hydrogen atom or C1-C6 alkyl group, n represents an integer of 0 to 6, R 2 represents a group —OR 3 or the like, and R 3 represents a hydrogen atom, C1-C6 alkyl group or the like, or R 1 and —(CH 2 ) n R 2 may bind to each other together with carbon atoms adjacent thereto through nitrogen atoms so as to form a spiro ring represented by the general formula (H): wherein R 41 is hydrogen, C1-C6 alkyl group or the like. The present compound has an excellent bactericidal action against Mycobacterium tuberculosis , multi-drug-resistant Mycobacterium tuberculosis , and atypical acid-fast bacteria.

  本发明提供了一种2,3-二氢-6-硝基咪唑并[2,1-b]噁唑化合物，其通式如下：其中，R1代表氢原子或C1-C6烷基，n代表0到6的整数，R2代表—OR3或类似的基团，R3代表氢原子、C1-C6烷基或类似的基团，或者R1和—(CH2)nR2可以通过相邻的碳原子通过氮原子结合在一起形成一个螺环，其通式为（H）：其中，R41为氢、C1-C6烷基或类似的基团。该化合物对结核分枝杆菌、多药耐药结核分枝杆菌和非典型酸性快速细菌具有优异的杀菌作用。