4-(5-methyl-4-imidazolyl)-3-thiabutanoic acid | 112528-37-7

• 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-methyl-4-imidazolyl)-3-thiabutanoic acid
• 英文别名: [(5-methyl-1H-imidazol-4-yl)methylsulfanyl]acetic acid；2-[(5-methyl-1H-imidazol-4-yl)methylsulfanyl]acetic acid
• CAS: 112528-37-7
• 化学式: C₇H₁₀N₂O₂S
• 分子量: 186.235
• InChiKey: UGQJJNIZHQVRIW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  91.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(5-methyl-4-imidazolyl)-3-thiabutanoic acid 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 生成 (5-Methyl-1H-imidazol-4-ylmethylsulfanyl)-acetyl chloride
  参考文献：
  名称：

  H2 抗组胺药，第 35 届 Mitt. 咪唑基甲硫基烷基取代的 1,2,4-三唑的合成和 H2 拮抗作用

  摘要：

  制备了单、二和三取代的 1,2,4-三唑衍生物并检查了组胺 H2 拮抗活性。

  DOI：

  10.1002/ardp.19873200613
• 作为产物：
  描述：

  巯基乙酸 、 4-羟甲基-5-甲基咪唑 以 溶剂黄146 为溶剂， 反应 24.0h， 以82%的产率得到4-(5-methyl-4-imidazolyl)-3-thiabutanoic acid
  参考文献：
  名称：

  酰基胍作为胍的生物等排体：NG酰化的咪唑基丙基胍，一种新型的组胺H2受体激动剂。

  摘要：

  N1-芳基（杂芳基）烷基-N2- [3-（1H-咪唑-4-基）丙基]胍是有效的组胺H2受体（H2R）激动剂，但由于缺乏口服生物利用度和CNS渗透性而削弱了它们的适用性。为了改善药代动力学，我们在胍基部分附近引入了羰基而不是亚甲基，从而将新型H2R激动剂的碱性降低了4-5个数量级。一些具有一个苯环的酰基胍比其二芳基类似物甚至更有效。如通过HPLC-MS证明的，酰基胍（烷基胍的生物等排体）从小鼠的肠中吸收并在脑中检测到。在使用重组受体的GTPase检测中，豚鼠的酰基胍比人的H2R更有力。在hH1R和hH3R处，这些化合物对中度拮抗剂或部分激动剂均弱。而且，确定了有效的部分hH4R激动剂。受体亚型的选择性取决于咪唑基丙基胍基团（特权结构），为包括强效H4R激动剂在内的独特药理学手段开辟了道路。

  DOI：

  10.1021/jm800841w

文献信息

• BONJEAN J.; SCHUNACK W., ARCH. PHARM., 320,(1987) N 6, 554-562
  作者：BONJEAN J.、 SCHUNACK W.

  DOI：——

  日期：——
• Neutral transition metal complexes with the tridentate ligand 4-(5-methyl-4-imidazolyl)-3-thiabutanoic acid. A series of isostructural octahedral compounds
  作者：Elisabeth Bouwman、Jan Reedijk

  DOI：10.1016/0020-1693(93)03681-y

  日期：1994.1

  The synthesis and spectroscopic properties of the iron, cobalt, nickel and copper complexes with the ligand 4-(5-methyl-4-imidazolyl)-3-thiabutanoic acid (abbreviated Hitba) are described. The compound Co(itba)(2) (A) crystallizes in the triclinic space group P $$($) over bar 1 with a = 7.600(1), b = 7.697(1), c = 8.2696(5) Angstrom, alpha = 86.745(8), beta = 71.321(7), gamma = 69.538(12)degrees, V = 428.5 Angstrom(3), D-x = 1.65 g/cm(3) for Z = 1. The compound Cu(itba)(2) (B) crystallizes in the triclinic group P $$($) over bar 1 with a = 7.789(3), b = 7.794(4), c = 8.138(4) Angstrom, alpha = 71.448(4), beta = 86.905(4), gamma = 67.805(4)degrees, V = 432.4 Angstrom(3), D-x = 1.66 g/cm(3) for Z = 1. In both structures the metal ion is located on the inversion centre because of symmetry considerations. The non-hydrogens were located using Fourier methods and the structures were refined by least-squares methods to residual R(w) values of 0.089 (A) and 0.050 (B). The coordination geometry of the metal ion in both compounds A and B is octahedral with the donor atoms of the two ligands in mutual irans positions. The bond distances in the cobalt compound are significantly different from those in the Jahn-Teller distorted copper compound (Co-N = 2.109(7), Cu-N = 1.986(3); Co-O = 2.065(6), Cu-O = 1.988(2); Co-S = 2.501(2), Cu-S = 2.7146(8)). The geometry of the cobalt ion can be described as a rather regular octahedron compared with the elongated octahedral copper structure. The obtained compounds M(itba)(2) are all isostructural according to their X-ray powder patterns and IR spectra, and all show remarkably strong ligand field spectra.