2-巯基-4-甲基咪唑 | 3247-70-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 中文名称: 2-巯基-4-甲基咪唑
• 中文别名: 2-氯甲基-5-(4-氯苯基)-1,3,4-噻二唑
• 英文名称: 2-mercapto-4-methylimidazole
• 英文别名: 4-methyl-1,3-dihydro-imidazole-2-thione；2-Mercapto-4(5)-methyl-imidazol；2-Mercapto-4-methyl-imidazol；4(5)-Methyl-2-imidazolethion；4-Methyl-2-imidazolethion；4-Methylimidazol-2-thiol；4-methyl-1,3-dihydroimidazole-2-thione
• CAS: 3247-70-9
• 化学式: C₄H₆N₂S
• 分子量: 114.171
• InChiKey: SBQPDLGIWJRKBS-UHFFFAOYSA-N

物化性质

• 熔点：
  247°C
• 沸点：
  165.4±23.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)
• 稳定性/保质期：
  遵照规定使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  56.2
• 氢给体数：
  2
• 氢受体数：
  1

安全信息

• 海关编码：
  2933290090

反应信息

• 作为反应物：
  描述：

  2-巯基-4-甲基咪唑 在 水 、 双氧水 作用下， 生成 4-methyl-1(3)H-imidazole-2-sulfonic acid
  参考文献：
  名称：

  Balaban; King, Journal of the Chemical Society, 1927, p. 1865

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(2-Sulfanylidene-1,3-dihydroimidazol-4-yl)acetic acid 生成 2-巯基-4-甲基咪唑
  参考文献：
  名称：

  671. 2-巯基乙二酸。第五部分。由氨基酸制备4（5）-取代的2-巯基乙二醛

  摘要：

  DOI：

  10.1039/jr9510003030

文献信息

• The toxicity of organic sulphides to the eggs and larvae of the glasshouse red spider mite. vii.—Benzyl phenyl sulphides (α-substituted)
  作者：J. E. Cranham、D. Greenwood、H. A. Stevenson

  DOI：10.1002/jsfa.2740090305

  日期：1958.3

  The synthesis of a number of benzyl phenyl sulphides, substituted in the α-position of the benzyl moiety, is described and their toxicities to the eggs and young mites of the glasshouse red spider (Tetranychus telarius L.) are tabulated.

  描述了许多苄基部分的 α 位取代的苄基苯基硫化物的合成，并列出了它们对温室红蜘蛛（Tetranychus telarius L.）的卵和幼螨的毒性。
• Imdazole systems. I. Imidzo[2,1-<i>b</i>][1,3,5]benzothiadiazepine derivatives as potential antipsychotic agents
  作者：Laurence Delia Vecchia、James Dellureficio、Biruta Kisis、Isidoros Vlattas

  DOI：10.1002/jhet.5570200528

  日期：1983.9

  Imidazo[2,1-b][1,3,5]benzothiadiazepine 3 constitutes a novel ring system, and its analogs 3a-i were synthesized to investigate their potential antipsychotic activity. The synthesis of the ring system was achieved by reaction of 2-aminophenylthioimidazoles 7 with phosgene or thiophosgene and by ring closure of the 1-[2-(2-imidazolyl)thiophenyliminocarbonyl]-1-piperazines 13. An efficient method for

  咪唑并[2,1- b ] [1,3,5]苯并噻二氮杂3构成一个新的环系统，并合成其类似物3a-i以研究其潜在的抗精神病活性。环系统的合成是通过2-氨基苯基硫代咪唑7与光气或硫光气的反应以及1- [2-（2-咪唑基）硫代苯基亚氨基羰基] -1-哌嗪13的闭环来实现的。对于硫脲的转化率的有效方法8,12胍3A经由对应cyanothioamidines 11,14被开发。
• Imidazole-Based pH-Sensitive Convertible Liposomes for Anticancer Drug Delivery
  作者：Ruiqi Huang、Vijay Gyanani、Shen Zhao、Yifan Lu、Xin Guo

  DOI：10.3390/ph15030306

  日期：——

  In efforts to enhance the activity of liposomal drugs against solid tumors, three novel lipids that carry imidazole-based headgroups of incremental basicity were prepared and incorporated into the membrane of PEGylated liposomes containing doxorubicin (DOX) to render pH-sensitive convertible liposomes (ICL). The imidazole lipids were designed to protonate and cluster with negatively charged phosphatidylethanolamine-polyethylene glycol when pH drops from 7.4 to 6.0, thereby triggering ICL in acidic tumor interstitium. Upon the drop of pH, ICL gained more positive surface charges, displayed lipid phase separation in TEM and DSC, and aggregated with cell membrane-mimetic model liposomes. The drop of pH also enhanced DOX release from ICL consisting of one of the imidazole lipids, sn-2-((2,3-dihexadecyloxypropyl)thio)-5-methyl-1H-imidazole. ICL demonstrated superior activities against monolayer cells and several 3D MCS than the analogous PEGylated, pH-insensitive liposomes containing DOX, which serves as a control and clinical benchmark. The presence of cholesterol in ICL enhanced their colloidal stability but diminished their pH-sensitivity. ICL with the most basic imidazole lipid showed the highest activity in monolayer Hela cells; ICL with the imidazole lipid of medium basicity showed the highest anticancer activity in 3D MCS. ICL that balances the needs of tissue penetration, cell-binding, and drug release would yield optimal activity against solid tumors.

  为了增强脂质体药物对实体肿瘤的活性，制备了三种新型脂质体，它们携带具有递增碱性的咪唑基头基，并被纳入PEG化脂质体膜中，其中含有多柔比星(DOX)，以形成pH敏感的可转换脂质体(ICL)。咪唑脂质体被设计为在pH从7.4降至6.0时质子化并与带负电荷的磷脂酰乙醇胺-聚乙二醇簇集，从而在酸性肿瘤间质中触发ICL。pH下降后，ICL表面带正电荷增多，在TEM和DSC中显示脂质相分离，并与细胞膜模拟模型脂质体聚集。pH下降还增强了由咪唑脂质体之一，sn-2-((2,3-二十六烷氧基丙基)硫基)-5-甲基-1H-咪唑构成的ICL中多柔比星的释放。ICL对单层细胞和几种3D MCS表现出比类似PEG化、pH不敏感的含多柔比星脂质体（作为对照和临床基准）更优越的活性。胆固醇的存在增强了ICL的胶体稳定性，但降低了它们的pH敏感性。咪唑脂质体中最基础的ICL在单层Hela细胞中表现出最高的活性；碱性中等的咪唑脂质体ICL在3D MCS中表现出最高的抗癌活性。平衡组织穿透、细胞结合和药物释放需求的ICL将产生最佳的实体肿瘤活性。
• Substituted Quinazoline or Pyridopyrimidine Derivative
  申请人：Mitsuya Morihiro

  公开号：US20080032996A1

  公开（公告）日：2008-02-07

  The present invention provides a compound having a glucokinase activating action being useful for prevention or treatment of diabetes mellitus, etc. being represented by the formula (I): X is nitrogen atom, etc.; Y is oxygen atom, etc.; R 1 is an optionally substituted five to six-membered heteroaryl group, etc.; R 2 is hydrogen atom or fluorine atom; and ring A is a monocyclic or bicyclic heteroaryl group which may have a substituent represented by the formula (II)] or a pharmaceutically acceptable salt thereof.

  本发明提供了一种具有激活葡萄糖激酶作用的化合物，该化合物可用于预防或治疗糖尿病等疾病，其表示式为(I)：其中，X为氮原子等；Y为氧原子等；R1为可选取代的五至六元杂环芳基基团等；R2为氢原子或氟原子；环A为单环或双环杂环芳基基团，其可具有由式(II)表示的取代基，或其药学上可接受的盐。
• Substituted quinazoline or pyridopyrimidine derivative
  申请人：Banyu Pharmaceutical Co., Ltd.

  公开号：US07687502B2

  公开（公告）日：2010-03-30

  The present invention provides a compound having a glucokinase activating action being useful for prevention or treatment of diabetes mellitus, etc. being represented by the formula (I): X is nitrogen atom, etc.; Y is oxygen atom, etc.; R1 is an optionally substituted five to six-membered heteroaryl group, etc.; R2 is hydrogen atom or fluorine atom; and ring A is a monocyclic or bicyclic heteroaryl group which may have a substituent represented by the formula (II)] or a pharmaceutically acceptable salt thereof.

  本发明提供了一种具有激活葡萄糖激酶作用的化合物，其表示为式（I）：X为氮原子等；Y为氧原子等；R1为可选取代的五到六元杂环芳基等；R2为氢原子或氟原子；环A为单环或双环杂环芳基，其可以具有由式（II）表示的取代基，或其药学上可接受的盐，用于预防或治疗糖尿病等。