4-[1H-imidazol-4-yl]-1-butyne | 223419-76-9

• 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-[1H-imidazol-4-yl]-1-butyne
• 英文别名: 4-(But-3-yn-1-yl)-1H-imidazole；5-but-3-ynyl-1H-imidazole
• CAS: 223419-76-9
• 化学式: C₇H₈N₂
• mdl: MFCD18632755
• 分子量: 120.154
• InChiKey: IGWFXUHNYJCMLQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.285
• 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：

  1-[1H-imidazol-4-yl]-5-amino-6-cyclohexyl-trans-3-hexene 、 盐酸 、 4-[1H-imidazol-4-yl]-1-butyne 生成 4-But-3-ynylimidazole HCl
  参考文献：
  名称：

  1H-4(5)-substituted imidazole derivatives

  摘要：

  本发明提供了一般式为：##STR1##的化合物，其中A为--NHCO--、--N(CH.sub.3)--CO--、--NHCH.sub.2--、--N(CH.sub.3)--CH.sub.2--、--CH.dbd.CH--、--COCH.sub.2--、CH.sub.2CH.sub.2--、--CH(OH)CH.sub.2--或--C.tbd.C--；X可以是H、CH.sub.3、NH.sub.2、NH(CH.sub.3)、N(CH.sub.3).sub.2、OH、OCH.sub.3、SH；R.sub.2为氢或甲基或乙基基团；R.sub.3为氢或甲基或乙基基团；n为0、1、2、3、4、5或6；R.sub.1选自以下组合的群：(a)烷基；(b)C.sub.3至C.sub.8环烷基；(c)苯基或取代苯基；(d)杂环；和(f)十氢萘或八氢萘基团；当R.sub.1和X一起表示5、6或6,6饱和双环环结构时，X可以是NH、O、S、SO.sub.2，当X被限制在5、6或6,6饱和的双环环结构中时，例如当X=dbd.NH时，R.sub.1和X一起表示直接连接到A的八氢吲哚环结构。

  公开号：

  US06166060A1
• 作为产物：
  描述：

  4-but-3-ynyl-1-(triphenylmethyl)imidazole 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以86%的产率得到4-[1H-imidazol-4-yl]-1-butyne
  参考文献：
  名称：

  Design, Synthesis, and Structure−Activity Relationships of Acetylene-Based Histamine H₃ Receptor Antagonists

  摘要：

  New, potent, and selective histamine H-3 receptor antagonists have been synthesized by employing the use of (1) an appropriately positioned nonpolar acetylene spacer group, (2) either a two-carbon straight chain linker or a conformationally restricting trans-cyclopropane ring between the C-4 position of an imidazole headgroup and the acetylene spacer, and (3) a Topliss operational scheme for side-chain substitution for optimizing the hydrophobic domain. Compounds 9-18 are examples synthesized with the two-carbon straight chain linker, whereas 26-31 are analogues prepared by incorporation of the trans-(+/-)-cyclopropane at the C-4 position of an imidazole headgroup. Synthesis of both the (1R,2R)- and (1S,2S)-cyclopropyl enantiomers of the most potent racemic compound 31 (K-i = 0.33 +/- 0.13 nM) demonstrated a stereopreference in H-3 receptor binding affinity for the (1R,2R) enantiomer 32 (K-i = 0.18 +/- 0.04 nM) versus the (1S,2S) enantiomer 33 (K-i = 5.3 +/- 0.5 nM). (1R,2R)-4-(2-(5,5-Dimethylhex-1-ynyl)cyclopropyl)- imidazole (32) is one of the most potent histamine H-3 receptor antagonists reported to date.

  DOI：

  10.1021/jm980310g

文献信息

• US6008240A
  申请人：——

  公开号：US6008240A

  公开（公告）日：1999-12-28
• US6166060A
  申请人：——

  公开号：US6166060A

  公开（公告）日：2000-12-26
• US6448282B1
  申请人：——

  公开号：US6448282B1

  公开（公告）日：2002-09-10
• Design, Synthesis, and Structure−Activity Relationships of Acetylene-Based Histamine H₃ Receptor Antagonists
  作者：Syed M. Ali、Clark E. Tedford、Rosilyn Gregory、Michael K. Handley、Stephen L. Yates、Walter W. Hirth、James G. Phillips

  DOI：10.1021/jm980310g

  日期：1999.3.1

  New, potent, and selective histamine H-3 receptor antagonists have been synthesized by employing the use of (1) an appropriately positioned nonpolar acetylene spacer group, (2) either a two-carbon straight chain linker or a conformationally restricting trans-cyclopropane ring between the C-4 position of an imidazole headgroup and the acetylene spacer, and (3) a Topliss operational scheme for side-chain substitution for optimizing the hydrophobic domain. Compounds 9-18 are examples synthesized with the two-carbon straight chain linker, whereas 26-31 are analogues prepared by incorporation of the trans-(+/-)-cyclopropane at the C-4 position of an imidazole headgroup. Synthesis of both the (1R,2R)- and (1S,2S)-cyclopropyl enantiomers of the most potent racemic compound 31 (K-i = 0.33 +/- 0.13 nM) demonstrated a stereopreference in H-3 receptor binding affinity for the (1R,2R) enantiomer 32 (K-i = 0.18 +/- 0.04 nM) versus the (1S,2S) enantiomer 33 (K-i = 5.3 +/- 0.5 nM). (1R,2R)-4-(2-(5,5-Dimethylhex-1-ynyl)cyclopropyl)- imidazole (32) is one of the most potent histamine H-3 receptor antagonists reported to date.
• 1H-4(5)-substituted imidazole derivatives
  申请人：Gliatech, Inc.

  公开号：US06166060A1

  公开（公告）日：2000-12-26

  The present invention provides, in its principal aspect, compounds of the general formula: ##STR1## when A is --NHCO--, --N(CH.sub.3)--CO--, --NHCH.sub.2 --, --N(CH.sub.3)--CH.sub.2 --, --CH.dbd.CH--, --COCH.sub.2 --, CH.sub.2 CH.sub.2 --, --CH(OH)CH.sub.2 -- or --C.tbd.C--; X can be H, CH.sub.3, NH.sub.2, NH(CH.sub.3),N(CH.sub.3).sub.2, OH, OCH.sub.3, SH, R.sub.2 is hydrogen or a methyl or ethyl group; R.sub.3 is hydrogen or a methyl or ethyl group; n is 0, 1, 2, 3, 4, 5 or 6; R.sub.1 is selected from the group consisting of (a) alkyl; (b) C.sub.3 to C.sub.8 cycloalkyl; (c) phenyl or substituted phenyl; (d) heteroocyclic; and (f) decahydronaphthalene or octahydroindane; and When R.sub.1 and X taken together denote a 5, 6 or 6, 6 saturated bicyclic ring structure, X can be NH, O, S, SO.sub.2, When X is constrained in a 5, 6 or 6, 6, saturated bicyclic ring structure, then for example, when X.dbd.NH, R.sub.1 and X taken together mean an octahydroindole ring structure directly attached to A.

  本发明提供了一般式为：##STR1##的化合物，其中A为--NHCO--、--N(CH.sub.3)--CO--、--NHCH.sub.2--、--N(CH.sub.3)--CH.sub.2--、--CH.dbd.CH--、--COCH.sub.2--、CH.sub.2CH.sub.2--、--CH(OH)CH.sub.2--或--C.tbd.C--；X可以是H、CH.sub.3、NH.sub.2、NH(CH.sub.3)、N(CH.sub.3).sub.2、OH、OCH.sub.3、SH；R.sub.2为氢或甲基或乙基基团；R.sub.3为氢或甲基或乙基基团；n为0、1、2、3、4、5或6；R.sub.1选自以下组合的群：(a)烷基；(b)C.sub.3至C.sub.8环烷基；(c)苯基或取代苯基；(d)杂环；和(f)十氢萘或八氢萘基团；当R.sub.1和X一起表示5、6或6,6饱和双环环结构时，X可以是NH、O、S、SO.sub.2，当X被限制在5、6或6,6饱和的双环环结构中时，例如当X=dbd.NH时，R.sub.1和X一起表示直接连接到A的八氢吲哚环结构。