1-(2-甲氧基苯基)-1H-咪唑-2-硫醇 | 51581-48-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 1-(2-甲氧基苯基)-1H-咪唑-2-硫醇
• 英文名称: N-(2-methoxyphenyl)-2-mercaptoimidazole
• 英文别名: 1-(2-methoxy-phenyl)-1,3-dihydro-imidazole-2-thione；1-o-Methoxyphenyl-2-mercaptoimidazol；1-(2-methoxyphenyl)-1H-imidazole-2-thiol；3-(2-methoxyphenyl)-1H-imidazole-2-thione
• CAS: 51581-48-7
• 化学式: C₁₀H₁₀N₂OS
• 分子量: 206.268
• InChiKey: MCLBGTWTHLDXJM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  56.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2-甲氧基苯基)-1H-咪唑-2-硫醇 以 甲醇 、 甲苯 为溶剂， 生成
  参考文献：
  名称：

  新型双（巯基咪唑基）（吡唑基）硼酸盐配体及其锌络合物化学

  摘要：

  制备了九个具有不同 3-R-巯基咪唑基部分的双（巯基咪唑基）（吡唑基）硼酸盐类型的新三足 NS2 配体作为它们的钾盐。用锌盐处理产生复合类型 L·Zn-Cl、L·Zn-I、L·Zn-ONO2、L·Zn-OClO3 和 [L·Zn(咪唑)]ClO4。试图形成 L·Zn-OH 或阳离子 L·Zn 复合物导致歧化和 ZnL2 复合物的形成。水解破坏产生一种[OZn4(thiooimidazolate)6]复合物。[L·Zn(C2H5OH)]+ 复合物可以成功模拟醇脱氢酶的酶-底物复合物中存在的 ZnS2NO 配位。L·Zn-X配合物在2-丙醇脱氢或对硝基苯甲醛加氢中表现出非常低的催化活性。新化合物通过总共 12 次结构测定得到鉴定。

  DOI：

  10.1002/ejic.200300079
• 作为产物：
  描述：

  异氰酸2-甲氧苯酯 在 盐酸 作用下， 以 甲苯 为溶剂， 反应 3.0h， 生成 1-(2-甲氧基苯基)-1H-咪唑-2-硫醇
  参考文献：
  名称：

  One-Pot Preparation of 1-Substituted Imidazole-2-thione from Isothiocyanate and Amino Acetal

  摘要：

  Isothiocyanates were treated with amino acetal and conc. HCl (0.5 eq.) successively in one-pot to afford 1-substituted imidazole-2-thiones in good yields.

  DOI：

  10.1080/00397919708007078

文献信息

• Synthesis of 2(1H)-Quinolinone Derivatives and Their Inhibitory Activity on the Release of 12(S)-Hydroxyeicosatetraenoic Acid (12-HETE) from Platelets.
  作者：Tetsuyuki UNO、Yasushi OZEKI、Yasuo KOGA、Gil-Namg CHU、Minoru OKADA、Katsumi TAMURA、Takehiro IGAWA、Fumiko UNEMI、Masaru KIDO、Takao NISHI

  DOI：10.1248/cpb.43.1724

  日期：——

  A search for potent inhibitors of release of 12(S)-hydroxyeicosatetraenoic acid (12-HETE), which plays an important role in the pathogenesis of various circulatory disorders and arteriosclerosis, led us to 6-[4-(1-cyclohexyl-5-tetrazolyl)butoxy]-3, 4-dihydro-2(1H)-quinolinone (cilostazol) and 2(1H)-quinoinone derivatives having an azole group in the side chain. Many 2(1H)-quinolilnone derivatives were synthesized and tested in vitro for the inhibitory activity in human platelets. 3, 4-Dihydro-6-[3-(1-o-tolylimidazol-2-yl)sulfinylpropoxy]-2(1H)-quinolinone (5k) was found to be one of the most potent inhibitors of 12-HETE release, being more potent than esculetin. In addition, the sulfoxide 5k showed in vivo inhibitory activity on platelet adhesion in rats. Since 5k is recemic, the enantiomers were prepared and their potencies were compared in vitro and in vivo. (S)-(+)-5k had the best pharmacological profile and was selected as a candidate drug for further development. The structure-activity relationships are discussed.

  寻找能够有效抑制12(S)-羟基二十碳四烯酸（12-HETE）释放的化合物，这种物质在多种循环系统疾病和动脉硬化的发病机制中扮演重要角色，最终引导我们发现了6-[4-(1-环己基-5-四唑基)丁氧]-3, 4-二氢-2(1H)-喹啉酮（西洛他唑）和含有唑类侧链的2(1H)-喹啉酮衍生物。合成了多种2(1H)-喹啉酮衍生物，并在体外测试了它们对人血小板的抑制活性。3, 4-二氢-6-[3-(1-邻甲基苯基咪唑-2-基)亚砜基丙氧]-2(1H)-喹啉酮（5k）是其中一种最有效的12-HETE释放抑制剂，其效能优于依斯可林。此外，亚砜化合物5k在大鼠体内表现出对血小板粘附的抑制活性。由于5k是外消旋体，因此合成了其对映体，并比较了它们在体外和体内的效能。 (S)-(+)-5k具有最佳的药理特性，并被选为进一步开发的候选药物。文中讨论了结构-活性关系。
• The best structural model of ADH so far: a pyrazolylbis(thioimidazolyl)borate zinc ethanol complex
  作者：Jan Seebacher、Mouhai Shu、Heinrich Vahrenkamp

  DOI：10.1039/b100281n

  日期：——

  [HB(timo-An)2(pzPh,Me)] − (L1) was combined with zinc perchlorate and ethanol to form the complex [L1·Zn(ethanol)]ClO4 which is the first zinc complex in which the N,S,S ligation of zinc and the attachment of ethanol occurring in the active center of horse liver alcoholdehydrogenase (ADH) have been reproduced; the structural details of the ZnNS2O coordination in the complex and in DMSO-inhibited ADH are in reasonably

  新的 N,S,S 配体 [HB(timo-An)2(pzPh,Me)] - (L1) 与高氯酸锌和乙醇结合形成络合物 [L1·Zn(乙醇)]ClO4，这是第一个锌复合物，其中锌的 N,S,S 连接和乙醇的连接发生在马肝乙醇脱氢酶 (ADH) 的活性中心；复合物中 ZnNS2O 配位的结构细节和 DMSO 抑制的 ADH 中的结构细节相当吻合。
• Orthogonal hydrogen/halogen bonding in 1-(2-methoxyphenyl)-1H-imidazole-2(3H)-thione-I2 adduct: An experimental and theoretical study
  作者：Hamdy S. El-Sheshtawy、Mohamed M. Ibrahim、Ibrahim El-Mehasseb、Maged El-Kemary

  DOI：10.1016/j.saa.2015.02.043

  日期：2015.5

  The molecular complex between 1-(2-methoxyphenyl)-1H-imidazole-2(3H)-thione (Hmim(OMe)) and iodine (I-2) was investigated. Single crystal of [(Hmim(OMe))center dot I-2] adduct was grown by slow evaporation technique from chloroform at room temperature. Spectroscopic techniques such as FT-IR and Raman techniques, as well as elemental and thermal analysis were used to characterize the complex. The crystal structure shows that the formed adduct stabilized by two noncovalent interactions, namely, hydrogen bond (HB) and halogen bond (XB). Orthogonal HB/XB associated with iodine atom (I) was observed and fully characterized. The ability of iodine to behave as hydrogen bond acceptor and halogen bond donor was held responsible for the orthogonal HB/XB presence. In addition, the structure of Hmim(OMe center dot)-I-2 was investigated theoretically using MP2/aug-cc-pVDZ level of theory. Natural bond orbital analysis (NBO) was used to investigate the molecular orbitals interactions and orbitals stabilization energies. (C) 2015 Elsevier B.V. All rights reserved.