1,4-二胍基丁烷 | 544-05-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 1,4-二胍基丁烷
• 中文别名: (S)-(+)联萘酚二(三氟甲磺酸酯 )
• 英文名称: arcaine
• 英文别名: Arcain；2-[4-(diaminomethylideneamino)butyl]guanidine
• CAS: 544-05-8
• 化学式: C₆H₁₆N₆
• 分子量: 172.233
• InChiKey: HGMDNMBBCKDWTQ-UHFFFAOYSA-N

物化性质

• 熔点：
  1722 HCl salt: 228
• 溶解度：
  Water (H2S salt, difficult), Ether (not easy)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  129
• 氢给体数：
  4
• 氢受体数：
  2

安全信息

• 海关编码：
  2925290090

反应信息

• 作为反应物：
  描述：

  1,4-二胍基丁烷 生成 四亚甲基二胺
  参考文献：
  名称：

  Linneweh, Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1931, vol. 200, p. 116

  摘要：

  DOI：
• 作为产物：
  描述：

  O-甲基异脲 、 alkaline earth salt of/the/ methylsulfuric acid 在 甲醇 作用下， 生成 1,4-二胍基丁烷
  参考文献：
  名称：

  Nakamura, Journal of Biochemistry, 1944, vol. 36, p. 251

  摘要：

  DOI：

文献信息

• Compound and method for the treatment of pain
  申请人：——

  公开号：US20030149042A1

  公开（公告）日：2003-08-07

  A compound, 7-chloro-4-hydroxy-2-(2-chloro-4-methylphenyl)-1,2,5,10-tetrahydropyridazino[4,5-b]quinoline-1,10-dione, pharmaceutically-acceptable salts thereof, a method for treating pain comprising administration of a pain-ameliorating effective amount of the compound and pharmaceutical compositions containing the compound are disclosed.

  本文披露了一种化合物，即7-氯-4-羟基-2-(2-氯-4-甲基苯基)-1,2,5,10-四氢吡啶并[4,5-b]喹啉-1,10-二酮，其药用可接受的盐，一种治疗疼痛的方法，包括给予该化合物的疼痛缓解有效量，并含有该化合物的药物组合物。
• Novel Compounds Containing Multiple Guanide Groups That Bind the HIV Coreceptor CXCR4
  作者：Royce A. Wilkinson、Seth H. Pincus、Joyce B. Shepard、Sarah K. Walton、Edward P. Bergin、Mohamed Labib、Martin Teintze

  DOI：10.1128/aac.00709-10

  日期：2011.1

  The G-protein-coupled receptor CXCR4 acts as a coreceptor for human immunodeficiency virus type 1 (HIV-1) infection, as well as being involved in signaling cell migration and proliferation. Compounds that block CXCR4 interactions have potential uses as HIV entry inhibitors to complement drugs such as maraviroc that block the alternate coreceptor CCR5 or in cancer therapy. The peptide T140, which contains five arginine residues, is the most potent antagonist of CXCR4 developed to date. In a search for nonpeptide CXCR4 ligands that could inhibit HIV entry, three series of compounds were synthesized from 12 linear and branched polyamines with 2, 3, 4, 6, or 8 amino groups, which were substituted to produce the corresponding guanidines, biguanides, or phenylguanides. The resulting compounds were tested for their ability to compete with T140 for binding to the human CXCR4 receptor expressed on mammalian cells. The most effective compounds bound CXCR4 with a 50% inhibitory concentration of 200 nM, and all of the compounds had very low cytotoxicity. Two series of compounds were then tested for their ability to inhibit the infection of TZM-bl cells with X4 and R5 strains of HIV-1. Spermine phenylguanide and spermidine phenylguanide inhibited infection by X4 strains, but not by R5 strains, at low micromolar concentrations. These results support further investigation and development of these compounds as HIV entry inhibitors.

  摘要 G 蛋白偶联受体 CXCR4 是人类免疫缺陷病毒 1 型（HIV-1）感染的核心受体，并参与细胞迁移和增殖的信号传递。阻断 CXCR4 相互作用的化合物有可能用作 HIV 进入抑制剂，以补充马拉维若等阻断替代核心受体 CCR5 的药物，或用于癌症治疗。多肽 T140 含有五个精氨酸残基，是迄今为止开发的最有效的 CXCR4 拮抗剂。在寻找可抑制 HIV 进入的非肽 CXCR4 配体的过程中，我们从 12 个含有 2、3、4、6 或 8 个氨基的线性和支链多胺中合成了三个系列的化合物，并将其取代以产生相应的胍类、双胍类或苯基胍类。测试了所得化合物与 T140 竞争结合哺乳动物细胞上表达的人类 CXCR4 受体的能力。最有效的化合物与 CXCR4 结合的 50% 抑制浓度为 200 nM，而且所有化合物的细胞毒性都很低。然后测试了两个系列的化合物抑制 TZM-bl 细胞感染 X4 和 R5 株 HIV-1 的能力。在低微摩尔浓度下，精胺苯胍和亚精胺苯胍能抑制 X4 株的感染，但不能抑制 R5 株的感染。这些结果支持进一步研究和开发这些化合物作为 HIV 进入抑制剂。
• The Synthesis of Bisguanidinoalkanes and Guanidinoalkanes, N- or N'-Substituted With Pyrimidines, as Analogues of Chlorhexidine
  作者：BC Elmes、G Holan、GT Wernert、DA Winkler

  DOI：10.1071/ch9960573

  日期：——

  A series of N,N???- alkanediylbis [N?-(5-halopyrimidin-2-yl)guanidine] salts has been synthesized along with N,N???-(trans-cyclohexane-1,4-diyl) bis [N'-(5-chloropyrimidin-2-yl)guanidine], N,N???-(cis-cyclohexane-1,4-diyl) bis [N?-(5-chloropyrimidin-2-yl)guanidine] dihydrochloride and N-(cis-4-amino-cyclohexan-1-yl)-N'-(5-chloropyrimidin-2-yl)guanidine dihydrochloride . Furthermore, a series of N-(alkan-1-yl)-N?-(5-chloropyrimidin-2yl)guanidine hydrochlorides and N-(6-aminohexan-1-yl)-N?-(5-chloropyrimidin-2-yl)guanidine dihydrochloride were synthesized. This series of compounds was prepared by displacement reactions of 2-methylsulfonylpyrimidines with bisguanidinoalkanes or by condensation of 5-chloro-2-cyanoaminopyrimidine (5-chloropyrimidin-2-ylcyanamide) with alkylamines .

  一系列N,N-烷基二亚甲基基[N-(5-卤代嘧啶-2-基)胍]盐类化合物已经合成，包括N,N-(反-环己烷-1,4-二基)二[N'-(5-氯代嘧啶-2-基)胍]、N,N-(顺-环己烷-1,4-二基)二[N-(5-氯代嘧啶-2-基)胍]二盐酸盐以及N-(顺-4-氨基环己基)-N'-(5-氯代嘧啶-2-基)胍二盐酸盐。此外，还合成了一系列N-(烷基-1-基)-N'-(5-氯代嘧啶-2-基)胍盐酸盐和N-(6-氨基己基)-N'-(5-氯代嘧啶-2-基)胍二盐酸盐。这些化合物是通过2-甲基磺酰基嘧啶与双胍基烷的取代反应或5-氯-2-氰基氨基嘧啶（5-氯代嘧啶-2-基氰胺）与烷基胺的缩合反应合成的。
• 1, 2, 5, 10-tetrahydropyridazino[4,5-b]quinoline-1,10-diones and their use for the treatment of pain
  申请人：——

  公开号：US20040053929A1

  公开（公告）日：2004-03-18

  Compounds according to structural diagram (I) are disclosed, wherein R 1 , A, E and D are as defined in the specification. Also disclosed are pharmaceutical compositions comprising a pain-ameliorating effective amount of a compound in accord with structural diagram (I).

  本发明揭示了根据结构图(I)的化合物，其中R1、A、E和D如规范中所定义。还揭示了包含符合结构图(I)的化合物的缓解疼痛有效量的药物组合物。
• 7-Chloro-4-hydroxy-2-(2-pyridylethyl)-1,2,5,10-tetrahydropyridazino[4,5-b]quinoline-1,10-dione and the use thereof for the treatment of pain
  申请人：——

  公开号：US20040053930A1

  公开（公告）日：2004-03-18

  A compound, 7-chloro-4-hydroxy-2-(2-pyridylethyl)-1,2,5,10-tetrahydropyridazino[4,5-b] quinoline-1,10-dione, its (−) enantiomer, its (+) enantiomer, pharmaceutically-acceptable salts thereof, a method for treating pain comprising administering a pain-ameliorating effective amount of the (−) enantiomer to an individual suffering from pain and pharmaceutical compositions containing the (−) enantiomer are disclosed.

  本发明涉及一种化合物，即7-氯-4-羟基-2-(2-吡啶基乙基)-1,2,5,10-四氢吡啶并[4,5-b]喹啉-1,10-二酮，其(−)对映体，其(+)对映体，其药学上可接受的盐，一种治疗疼痛的方法，包括向遭受疼痛的个体投与(−)对映体的止痛有效量，以及含有(−)对映体的制药组合物。