2-(1H-苯并咪唑-2-基硫代)-乙醇 | 7673-83-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 中文名称: 2-(1H-苯并咪唑-2-基硫代)-乙醇
• 英文名称: 2-(2-hydroxyethylthio)-1H-benzimidazole
• 英文别名: 2-(2-benzimidazoylthio)ethanol；2-(1H-benzoimidazol-2-ylsulfanyl)-ethanol；2-(1H-benzimidazol-2-ylmercapto)-ethanol；2-(1H-Benzimidazol-2-ylmercapto)-aethanol；2-<β-Hydroxy-aethylmercapto>-benzimidazol；2-(2-Hydroxyethylthio)benzimidazole；2-(1H-benzimidazol-2-ylsulfanyl)ethanol
• CAS: 7673-83-8
• 化学式: C₉H₁₀N₂OS
• mdl: MFCD00463759
• 分子量: 194.257
• InChiKey: HFDPECWVRWDXHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  74.2
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  2-(1H-苯并咪唑-2-基硫代)-乙醇 在 氯化亚砜 作用下， 生成 2-(2-chloro-ethylsulfanyl)-1H-benzoimidazole
  参考文献：
  名称：

  Nakajima et al., Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1958, vol. 78, p. 1378,1381

  摘要：

  DOI：
• 作为产物：
  描述：

  邻苯二胺 在 potassium carbonate 、 potassium hydroxide 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 7.0h， 生成 2-(1H-苯并咪唑-2-基硫代)-乙醇
  参考文献：
  名称：

  Expression, Purification, and Comparative Inhibition of Helicobacter pylori Urease by Regio-Selectively Alkylated Benzimidazole 2-Thione Derivatives

  摘要：

  尿素酶酶是发现有效药物和农业产品的重要目标。设计了十三种区域选择性烷基化苯并二唑-2-硫酮衍生物，以携带尿素酶抑制剂的必要特征。利用His标签法从幽门螺杆菌中分离出重组尿素酶。使用色谱和FPLC技术纯化和表征分离的酶，显示最大活性为200毫克/毫升。此外，还购买了商业的菜豆尿素酶，并包括在这项研究中进行比较和机制研究。合成了设计的化合物，并对它们在两种尿素酶中的抑制活性进行了筛选。化合物2抑制幽门螺杆菌和菜豆尿素酶的IC50值分别为0.11和0.26毫摩尔/升。而化合物5的IC50值分别为0.01和0.29毫摩尔/升。化合物2和5被对接到幽门螺杆菌尿素酶（PDB ID：1E9Y；分辨率：3.00 Å）中，并展示正确的结合模式，自由能（ΔG）值分别为-9.74和-13.82 kcal mol−1。此外，2和5的in silico ADMET和毒性属性表明它们的一般安全性和可用作药物的可能性。最后，通过对成纤维细胞的体外细胞毒性实验验证了这些化合物的安全性。

  DOI：

  10.3390/molecules27030865

文献信息

• Studies on Antiulcer Agents. III. Plausible Mechanism of Antisecretory Action of Ethyl 2-((1H-Benzimidazol-2-yl)sulfinylmethyl)-4-dimethylamino-5-pyrimidinecarboxylate, an H+/K+-ATPase Inhibitor, Based on Its Reaction with Thiols.
  作者：Kohji TERASHIMA、Osamu MURAOKA、Masaru ONO

  DOI：10.1248/cpb.43.1985

  日期：——

  hylidenamino]pyrimido[1,2-a]benzimid azole-3- carboxylate (6), instead of providing a disulfide of type 3, 2-(2-alkyldithiomethylpyridino)benzimidazolide, the product predicted to be formed according to the reaction mechanism of common H+/K(+)-ATPase inhibitors, such as omeprazole or lansoprazole, with mercaptans. With a large excess of 2-mercaptoethanol, 5 provided 2-(2-hydroxyethylthio)-1H-benzimidazole

  探讨2-[（（1H-苯并咪唑-2-基）亚磺酰基甲基] -4-二甲基氨基-5-嘧啶羧酸乙酯（5）（一种潜在的H + / K（+）-ATPase抑制剂）在胃中的抗分泌活性机制。在壁细胞的酸性区室中，研究了其与一些烷基硫醇在盐酸存在下的反应。在酸性条件下用2-巯基乙醇处理后，得到5的特征1：2加合物，乙基4- [2-（2-羟乙基二硫基）-1-（2-羟乙基硫基）亚乙基氨基]嘧啶基[1,2-a]苯并咪唑-3-羧酸盐（6）代替提供3型2-（2-烷基二硫甲基吡啶基）苯并咪唑啉的二硫键，而是根据常见的H + / K（+）-ATPase抑制剂的反应机理预测形成的产物，例如如奥美拉唑或兰索拉唑，与硫醇。大量过量的2-巯基乙醇
• Mechanism of Inhibition of H+, K+-ATPase by Sodium 2-((4-(3-Methoxypropoxy)-3-methylpyridin-2-yl)methylsulfinyl)-lH- benzimidazole (E3810).
  作者：Shigeharu NOCHI、Yumi YOKOYAMA、Megumi NARUKAWA、Kumiko EBINE、Miho MURAHASHI、Yoshiyuki KAWAKAMI、Naoki ASAKAWA、Tadashi SATO

  DOI：10.1248/cpb.44.552

  日期：——

  Sodium 2-[[4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methylsulfinyl]-1H-benzimidazole (E3810) and omeprazole inhibit gastric acid secretion through inhibition of the activity of H+, K+-ATPase present in parietal cell membrane vesicles, by chemical modification of SH groups in the enzyme molecule. In order to clarify the mechanism of the chemical modification, reaction products of E3810 and omeprazole with 2-mercaptoethanol under acidic conditions (pH 3, 4, 5, 6) were isolated by HPLC, and subjected to structural analysis by UV, 1H-NMR and mass spectrometry. E3810 and omeprazole appeared to undergo two kinds of reactions, affording disulfide-type products (type I reaction) and sulfide-type products (type II reaction). The rates of these reactions were determined by HPLC, and the stability of the products in the presence and absence of glutathione was investigated. In the case of E3810, type I reaction was found to proceed faster than type II reaction at every pH value studied. The type I reaction of E3810 was faster than that of comeprazole. The rate of type I reaction decreased at pH 5 and 6, especially for omeprazole, and the contribution of type II reaction increased as the pH of the reaction mixture was increased. The sulfide-type modification products were stable, whereas the formation of the disulfide-type modification products was reversed by the action of endogenous SH compounds such as glutathione. These results suggest that higher inhibitory activity of E3810 against gastric acid secretion and facter recovery of the enzyme activity after inhibition by E3810 can be expencted, as compared with those of omeprazole.

  2-[[4-(3-甲氧基丙氧基)-3-甲基吡啶-2-基]甲基亚磺酰基]-1H-苯并咪唑钠（E3810）和奥美拉唑通过抑制壁细胞膜囊泡中H+、K+-ATP酶的活性来抑制胃酸分泌，其作用机理是化学修饰酶分子中的SH基团。为了阐明化学修饰的机理，通过HPLC分离了E3810和奥美拉唑与2-巯基乙醇在酸性条件（pH 3、4、5、6）下的反应产物，并通过紫外光谱、1H-NMR和质谱对其进行了结构分析。E3810和奥美拉唑似乎经历了两种反应，产生了二硫键型产物（I型反应）和硫键型产物（II型反应）。通过HPLC测定了这些反应的速率，并研究了产物在有和没有谷胱甘肽时的稳定性。就E3810而言，在研究的每个pH值下，I型反应都比II型反应进行得快。E3810的I型反应比奥美拉唑的I型反应快。在pH 5和6时，I型反应的速率降低，特别是对于奥美拉唑而言，并且随着反应混合物的pH升高，II型反应的贡献增加。硫键型
• Knobloch et al., Archiv der Pharmazie, 1958, vol. 291, p. 113,114
  作者：Knobloch et al.

  DOI：——

  日期：——
• ACTIVE SUBSTANCE AND PHARMACEUTICAL COMPOSITION FOR TREATING ALCOHOL DEPENDENCE, AND A METHOD FOR OBTAINING AND THE USE OF SAID ACTIVE SUBSTANCE
  申请人：Ivashchenko Andrey Alexandrovich

  公开号：US20110245231A1

  公开（公告）日：2011-10-06

  The invention relates to novel drug substance for the treatment of alcohol dependence, pharmaceutical composition, medicament and method for treatment of dependence on using ethyl alcohol containing beverages. The invention provides a drug substance for treating alcohol dependence in human and warm-blooded animals representing substituted 1H-benzimidazoles of the general formula 1 or pharmaceutically acceptable salts and/or hydrates thereof wherein: W represents S or S═0 group; R 1 represents one or more substituent selected from hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, optionally substituted azaheterocyclyl; R 2 represents hydrogen or optionally substituted C 1 -C 4 alkyl; R 3 and R 4 independently represent optionally identical substituents selected from hydrogen or optionally substituted C 1 -C 4 alkyl; R 5 represents an alkyl substituent selected from hydrogen, optionally substituted C 1 -C 7 alkyl, optionally substituted aryl, optionally substituted heterocyclyl, C 1 -C 4 alkoxycarbonyl, optionally substituted aminocarbonyl.
• Nakajima et al., Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1958, vol. 78, p. 1378,1381
  作者：Nakajima et al.

  DOI：——

  日期：——