4(5)-(3-chloropropyl)imidazole | 84157-77-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4(5)-(3-chloropropyl)imidazole
• 英文别名: 4-(3-chloro-propyl)-1(3)H-imidazole；4-(3-Chlor-propyl)-1(3)H-imidazol；3-(1H-imidazol-4-yl)propyl chloride；5-(3-chloropropyl)-1H-imidazole
• CAS: 84157-77-7
• 化学式: C₆H₉ClN₂
• mdl: MFCD19216572
• 分子量: 144.604
• InChiKey: ZBLBZGRRACOZRJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4(5)-(3-chloropropyl)imidazole 在 Rh on carbon 盐酸 、 氨 、 氢气 作用下， 以 乙二醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 235.0h， 生成 5-Cyclohexyl-2-[3-(3H-imidazol-4-yl)-propyl]-1H-imidazole
  参考文献：
  名称：

  Synthesis and biological assays of new H3-antagonists with imidazole and imidazoline polar groups

  摘要：

  New histamine H-3-receptor antagonists were synthesised and tested on rat brain membranes and on electrically stimulated guinea-pig ileum. The new compounds have a central polar group represented by a 2-alkylimidazole or a 2-thioimidazoline nucleus. The effect of the polar group basicity on the optimal length of the alkyl chain, connecting this group to a 4(5)-imidazolyl ring, was investigated. The best affinity values, obtained by displacement of [H-3]-RAMHA from rat brain, were obtained for the 2-alkylimidazole derivatives (2a-f) with tetramethylene chain (pK(i) 8.03-8.97), having an intermediate basicity between that of the previously reported 2-thioimidazoles (1a-i) and that of 2-alkylthioimidazolines (3a-h). In contrast, a general lowering of affinity (pK(i) 5.90-7.63) was observed for compounds of the last series (3a-h), with a complex dependence on the terminal lipophilic group and chain length. (C) 2000 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(99)00115-9
• 作为产物：
  描述：

  4-(3-羟丙基)咪唑草酸盐 在 氯化亚砜 作用下， 生成 4(5)-(3-chloropropyl)imidazole
  参考文献：
  名称：

  Pasini; Coda, Gazzetta Chimica Italiana, 1957, vol. 87, p. 1464,1473

  摘要：

  DOI：

文献信息

• Imidazole compounds and their therapeutic applications
  申请人：Institut National de la Sante et de la Recherche Medicale

  公开号：US05559113A1

  公开（公告）日：1996-09-24

  A compound selected from the group consisting of a compound of the formula ##STR1## wherein the substituents are defined as in the specification having antagonist properties to histamine H.sub.3 -receptors.

  从以下化合物组合中选择的一种化合物，其化学式为##STR1##其中取代基的定义如规范中所述，具有对组织胺H.sub.3受体的拮抗性能。
• The role of HB-donor groups in the heterocyclic polar fragment of H3-antagonists.
  作者：Valentina Zuliani、Fabrizio Bordi、Mirko Rivara、Claudia Silva、Federica Vacondio、Giovanni Morini、Silvia Rivara、Elisabetta Barocelli、Vigilio Ballabeni、Simona Bertoni、Francesca Magnanini、Pier Vincenzo Plazzi

  DOI：10.1016/s0014-827x(03)00147-2

  日期：2003.9

  best affinity values were obtained with di-methylene chains. Moreover, N-methylation at the 2-aminobenzimidazole moiety 13-16 revealed different behaviour for compounds having different spacer lengths. In fact, methylation of the exocyclic NH group maintained high affinity for the tri-methylene 2-aminobenzimidazole derivative, while a drop in affinity was observed for the annular N-methylation. An opposite

  最近有报道说，由咪唑组成的化合物通过烷基间隔基与2-氨基苯并咪唑连接，对H（3）-受体表现出高亲和力。2-氨基苯并咪唑的胍片段可能与结合位点的氢键相互作用有关，被称为“极性片段”。在目前的工作中，我们从具有二亚甲基间隔基1（pK（i）= 7.25）或三亚甲基1 2（pK（i）= 8.90）的2-氨基苯并咪唑衍生物开始，我们研究了氢键的重要性（HB）供体基团在与H（3）-受体相互作用的极性片段上。用不同的部分取代2-氨基苯并咪唑[2-氨基苯并噻唑，3，4; 2-硫代苯并咪唑，5，6; 2-硫代苯并噻唑，7，8; 2-硫基-4-苯基或2-硫基-5-苯基-N-甲基咪唑，[9-12]强调了极性基团碱性对烷基链最佳长度的影响：较长的间隔基优选具有中等碱性的极性基团，而在存在中性极性基团的情况下，采用亚甲基链。此外，对于具有不同间隔长度的化合物，在2-氨基苯并咪唑部分13-16处的N-甲基化显示出不同
• Bicyclic guanidines
  申请人：Imperial Chemical Industries PLC

  公开号：US04463005A1

  公开（公告）日：1984-07-31

  The invention relates to bicyclic derivatives which are histamine H-2 antagonists and which inhibit gastric acid secretion. According to the invention there is provided a guanidine derivative of the formula I: ##STR1## in which R.sup.1 and R.sup.2, same or different, are hydrogen or 1-10C alkyl, 3-8C cycloalkyl or 4-14C cycloalkylalkyl, each alkyl, cycloalkyl or cycloalkylalkyl optionally carrying one or more F, Cl or Br atoms, provided that one of R.sup.1 and R.sup.2 is halogen substituted, or R.sup.2 is hydrogen and R.sup.1 is R.sup.3 -E-W in which W is 2-6C alkylene optionally substituted by 1 or 2 1-4C alkyls, E is O, S, SO, SO.sub.2 or NR.sup.4 in which R.sup.4 is H or 1-6C alkyl, R.sup.3 is H or 1-6C alkyl optionally substituted by 1 or 2 1-4C alkyls, or R.sup.3 and R.sup.4 are joined to form a pyrrolidine, piperidine, morpholine, piperazine or N-methylpiperazine ring, or R.sup.2 is H and R.sup.1 is H, 1-10C alkyl, 3-8C cycloalkyl, 4-14C cycloalkylalkyl, 3-6C alkenyl, 3-6C alkynyl, 1-6C alkanoyl, 6-10C aryl, 7-11C aralkyl or 7-11C aroyl; ring X is a heterocyclic ring as defined in the specification; A is phenylene or 5-7C cycloalkylene, or a 1-8 C alkylene into which is optionally inserted one or two groups; ring Y is a heterocyclic ring described in the specification: and the pharmaceutically-acceptable acid-addition salts thereof. Manufacturing processes and pharmaceutical compositions are also described.

  本发明涉及一种双环衍生物，其为组胺H-2拮抗剂并抑制胃酸分泌。根据本发明提供了式I的鸟氨酸衍生物：##STR1## 其中R1和R2，相同或不同，是氢或1-10C烷基，3-8C环烷基或4-14C环烷基烷基，每个烷基，环烷基或环烷基烷基可以携带一个或多个F，Cl或Br原子，前提是R1和R2中的一个是卤素取代的，或者R2为氢，R1为R3-E-W，其中W为2-6C烷基烯，可选择地被1或2个1-4C烷基取代，E为O，S，SO，SO.sub.2或NR.sup.4，其中R.sup.4为H或1-6C烷基，R.sup.3为H或1-6C烷基，可选择地被1或2个1-4C烷基取代，或者R.sup.3和R.sup.4连接形成吡咯烷，哌嗪，吗啉，哌嗪或N-甲基哌嗪环，或者R2为H，R1为H，1-10C烷基，3-8C环烷基，4-14C环烷基烷基，3-6C烯基，3-6C炔基，1-6C烷酰基，6-10C芳基，7-11C芳烷基或7-11C芳酰基；环X是规范中定义的杂环；A是苯基或5-7C环烷基，或者是插入了一两个基团的1-8C烷基；环Y是规范中描述的杂环；以及其药学上可接受的酸盐。还描述了制造过程和制药组合物。
• Imidazole derivatives for pharmaceutical use
  申请人：Institut National de la Sante et de la Recherche Medicale

  公开号：US05708171A1

  公开（公告）日：1998-01-13

  A compound selected from the group consisting of a compound of the formula ##STR1## having antagonist properties to histamine H.sub.3 -receptors.

  从以下化合物组中选择的一种化合物，具有对组胺H.sub.3受体的拮抗作用的化合物，其化学式为##STR1##。
• Bicyclic derivatives
  申请人：IMPERIAL CHEMICAL INDUSTRIES PLC

  公开号：EP0060730A2

  公开（公告）日：1982-09-22

  The invention relates to bicyclic derivatives which are histamine H-2 antagonists and which inhibit gastric acid secretion. According to the invention there is provided a guanidine derivative of the formula I: in which R1 and R2, same or different, are hydrogen or 1-10C alkyl, 3-8C cycloalkyl or 4-14C cycloalkylalkyl, each alkyl, cycloalkyl or cycloalkylalkyl optionally carrying one or more F, Cl or Br atoms, provided that one of R1 and R2 is halogen substituted, or R2 is hydrogen and R1 is R3-E-W in which W is 2-6C alkylene optionally substituted by 1 or 2 1-4C alkyls, E is 0, S, SO, S02 or NR4 in which R4 is H or 1-6C alkyl, R3 is H or 1-6C alkyl optionally substituted by 1 or 2 1-4C alkyls, or R3 and R4 are joined to form a pyrrolidine, piperidine, morpholine, piperazine or N-methylpiperazine ring, or R2 is H and R1 is H, 1-10C alkyl, 3-8C cycloalkyl, 4-14C cycloalkylalkyl, 3-6C alkenyl, 3-6C alkynyl, 1-6C alkanoyl, 6-10C aryl, 7-11C aralkyl or 7-11C aroyl; ring X is a heterocyclic ring as defined in the specification; A is phenylene or 5-7C cycloalkylene, or a 1-8C alkylene into which is optionally inserted one or two groups; ring Y is a heterocyclic ring described in the specification: and the pharmaceutically-acceptable acid-addition salts thereof. Manufacturing processes and pharmaceutical compositions are also described.

  本发明涉及组胺 H-2 拮抗剂和抑制胃酸分泌的双环衍生物。根据本发明，提供了一种式 I 的胍衍生物： 其中 R1 和 R2 相同或不同，为氢或 1-10C 烷基、3-8C 环烷基或 4-14C 环烷基烷基，每个烷基、环烷基或环烷基烷基可选带一个或多个 F、Cl 或 Br 原子，条件是 R1 和 R2 之一被卤素取代，或 R2 为氢，R1 为 R3-E-W，其中 W 为可选被 1 或 2 个 1-4C 烷基取代的 2-6C 亚烷基，E 为 0、S、SO、S02或NR4，其中R4是H或1-6C烷基，R3是H或1-6C烷基，可选择被1或2个1-4C烷基取代，或R3和R4连接形成吡咯烷、哌啶、吗啉、哌嗪或N-甲基哌嗪、或 R2 为 H，R1 为 H、1-10C 烷基、3-8C 环烷基、4-14C 环烷基、3-6C 烯基、3-6C 烷炔基、1-6C 烷酰基、6-10C 芳基、7-11C 芳基或 7-11C 芳基；环 X 是说明书中定义的杂环； A 是亚苯基或 5-7C 环亚烷基，或 1-8C 亚烷基，其中可选择插入一个或两个基团； 环 Y 是说明书中描述的杂环：及其药学上可接受的酸加成盐。还描述了制造工艺和药物组合物。