2,2'-dithio-di-(1-methyl-imidazole) | 61747-29-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2,2'-dithio-di-(1-methyl-imidazole)
• 英文别名: bis(1-methylimidazol-2-yl) disulphide；N-methylimidazolyl disulfide；bis(1-methyl-1H-imidazole-2-yl)disulfide；1,1'-dimethyl-1H,1'H-2,2'-disulfanediyl-bis-imidazole；bis-(1-methyl-1H-imidazol-2-yl)-disulfide；Bis-(1-methyl-1H-imidazol-2-yl)-disulfid；bis(1-methylimidazol-2-yl)disulfide；1H-Imidazole, 2,2'-dithiobis[1-methyl-；1-methyl-2-[(1-methylimidazol-2-yl)disulfanyl]imidazole
• CAS: 61747-29-3
• 化学式: C₈H₁₀N₄S₂
• 分子量: 226.326
• InChiKey: VWGKCNYHKYTHBR-UHFFFAOYSA-N

物化性质

• 熔点：
  138 °C
• 沸点：
  457.8±28.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  86.2
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P305+P351+P338,P330,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H302,H312,H315,H319,H332,H335

反应信息

• 作为反应物：
  描述：

  2,2'-dithio-di-(1-methyl-imidazole) 以25%的产率得到
  参考文献：
  名称：

  COREY E. J.; BRUNELLE D. J., TETRAHEDRON LETT. , 1976, NO 38, 3409-3412

  摘要：

  DOI：
• 作为产物：
  描述：

  甲巯咪唑 在 碘 、 三甲胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.92h， 以74%的产率得到2,2'-dithio-di-(1-methyl-imidazole)
  参考文献：
  名称：

  软蝎子氢化三（2-巯基-1-甲基咪唑基）硼酸酯）氧化钨和硫基络合物作为乙炔水合酶模型。

  摘要：

  一系列具有富硫配体氢化三(2-巯基-1-甲基咪唑基)硼酸酯) (Tm Me ) 的 W IV炔配合物作为仿生模型被提出，以阐明钨酶乙炔水合酶 (AH) 的机制。单炔和/或双炔前体与NaTm Me反应，所得络合物[W(CO)(C 2 R 2 )(Tm Me )Br](R=H 1 , Me 2 )被氧化为目标物[ WE(C 2 R 2 )(Tm Me )Br] (E=O, R=H 4 , Me 5 ; E=S, R=H 6 , Me 7 ) 使用吡啶-N-氧化物和甲基硫杂丙环。在 MeCN 中用 TlOTf 萃取卤化物得到阳离子配合物 [WE(C 2 R 2 )(MeCN)(Tm Me )](OTf) (E=CO, R=H 10 , Me 11 ; E=O, R=H 12 ，Me 13 ；E=S，R=H 14 ，Me 15 )。没有 MeCN，双核配合物 [W 2 O(μ-O)(C 2 Me 2

  DOI：

  10.1002/chem.202001127

文献信息

• Soft Scorpionate Hydridotris(2‐mercapto‐1‐methylimidazolyl) borate) Tungsten‐Oxido and ‐Sulfido Complexes as Acetylene Hydratase Models
  作者：Carina Vidovič、Ferdinand Belaj、Nadia C. Mösch‐Zanetti

  DOI：10.1002/chem.202001127

  日期：2020.9.25

  one molecule of C2Me2. This provides evidence that a fine balance of the softness at W is important for acetylene coordination. Upon dissolving complex 8 in acetonitrile complex 13 is reconstituted in contrast to 9. All complexes exhibit the desired stability toward water and the observed effective coordination of the scorpionate ligand avoids decomposition to disulfide, an often‐occurring reaction in

  一系列具有富硫配体氢化三(2-巯基-1-甲基咪唑基)硼酸酯) (Tm Me ) 的 W IV炔配合物作为仿生模型被提出，以阐明钨酶乙炔水合酶 (AH) 的机制。单炔和/或双炔前体与NaTm Me反应，所得络合物[W(CO)(C 2 R 2 )(Tm Me )Br](R=H 1 , Me 2 )被氧化为目标物[ WE(C 2 R 2 )(Tm Me )Br] (E=O, R=H 4 , Me 5 ; E=S, R=H 6 , Me 7 ) 使用吡啶-N-氧化物和甲基硫杂丙环。在 MeCN 中用 TlOTf 萃取卤化物得到阳离子配合物 [WE(C 2 R 2 )(MeCN)(Tm Me )](OTf) (E=CO, R=H 10 , Me 11 ; E=O, R=H 12 ，Me 13 ；E=S，R=H 14 ，Me 15 )。没有 MeCN，双核配合物 [W 2 O(μ-O)(C 2 Me 2
• Radical–nucleophilic substitution (S_RN1) reactions. Part 2. Preparation and reactions of α-nitrosulphides
  作者：W. Russell Bowman、Devajvoti Rakshit、Michael D. Valmas

  DOI：10.1039/p19840002327

  日期：——

  to the anion of 2-nitropropane, SN2 attack of the anion of 2-nitropropane on symmetrical disulphides, and SRN1 reaction of 2-substituted-2-nitropropanes with thiolate anions. The α-nitrosulphides undergo SRN1 substitution with the anion of 2-nitropropane, and SRN1 substitution or redox reactions with thiolate anions. The electron spin resonance (e.s.r.) spectrum of the radical-anion of 1-methyl-1-nitroethyl

  一系列α-亚硝基硫化物[Me 2 C（SR）NO 2，其中R = 2-吡啶基，嘧啶-2-基，1,3-苯并噻唑-2-基，1-甲基咪唑-2-基和4， 5-二氢-1,3-噻唑-2-基]已经制备由氧化加成硫醇盐阴离子的至2-硝基丙烷的阴离子，小号ñ 2 2-硝基丙烷的上对称二硫化物的阴离子的攻击，和小号RN 1 2-取代-2-硝基丙烷与硫醇根阴离子的反应 α-亚硝基硫经过2-硝基丙烷阴离子和S RN的S RN 1取代1与硫醇根阴离子的取代或氧化还原反应。已经观察到1-甲基-1-硝基乙基嘧啶-2-基硫醚的自由基阴离子的电子自旋共振（esr）光谱。
• Inhibitors of HIV reverse transcriptase
  申请人：Merck & Co., Inc.

  公开号：US05527819A1

  公开（公告）日：1996-06-18

  Novel indole compounds inhibit HIV reverse transcriptase, and are useful in the prevention or treatment of infection by HIV and the treatment of AIDS, either as compounds, pharmaceutically acceptable salts, pharmaceutical composition ingredients, whether or not in combination with other antivirals, anti-infectives, immunomodulators, antibiotics or vaccines. Methods of treating AIDS and methods of preventing or treating infection by HIV are also described.

  新型吲哚化合物抑制HIV逆转录酶，在预防或治疗HIV感染以及治疗艾滋病方面具有用途，无论是作为化合物、药学上可接受的盐、药物组成成分，还是与其他抗病毒药物、抗感染药物、免疫调节剂、抗生素或疫苗结合使用。还描述了治疗艾滋病和预防或治疗HIV感染的方法。
• Electrochemical Synthesis of Imidazolyl Disulfides
  作者：Fillmore Freeman、Monica C. Keindl、Henry N. Po、Elizabeth Brinkman、Jeffrey A. Masse

  DOI：10.1055/s-1989-27371

  日期：——

  Imidazole-2(3H)-thione (1a), 4,5-diphenylimidazole-2(3H)-thione (1b), 1-methylimidazole-2(3H)-thione (1c, mercaptazole, mercazolyl, methimazole), benzimidazole-2(3H)-thione (1d) and 5-methylbenzimidazole- 2(3H)-thione (1e) are electrochemically oxidized to the corresponding disulfides 2a-e, respectively.

  咪唑-2(3H)-硫酮(1a)、4,5-二苯基咪唑-2(3H)-硫酮(1b)、1-甲基咪唑-2(3H)-硫酮(1c、硫醇、硫唑基、甲硫咪唑)、苯并咪唑- 2(3H)-硫酮(1d)和5-甲基苯并咪唑-2(3H)-硫酮(1e)分别被电化学氧化成相应的二硫化物2a-e。
• Development of disulfide-derived fructose-1,6-bisphosphatase (FBPase) covalent inhibitors for the treatment of type 2 diabetes
  作者：Yi-xiang Xu、Yun-yuan Huang、Rong-rong Song、Yan-liang Ren、Xin Chen、Chao Zhang、Fei Mao、Xiao-kang Li、Jin Zhu、Shuai-shuai Ni、Jian Wan、Jian Li

  DOI：10.1016/j.ejmech.2020.112500

  日期：2020.10

  Fructose-1,6-bisphosphatase (FBPase), as a key rate-limiting enzyme in the gluconeogenesis (GNG) pathway, represents a practical therapeutic strategy for type 2 diabetes (T2D). Our previous work first identified cysteine residue 128 (C128) was an important allosteric site in the structure of FBPase, while pharmacologically targeting C128 attenuated the catalytic ability of FBPase. Herein, ten approved cysteine covalent drugs were selected for exploring FBPase inhibitory activities, and the alcohol deterrent disulfiram displayed superior inhibitory efficacy among those drugs. Based on the structure of lead compound disulfiram, 58 disulfide-derived compounds were designed and synthesized for investigating FBPase inhibitory activities. Optimal compound 3a exhibited significant FBPase inhibition and glucose-lowering efficacy in vitro and in vivo. Furthermore, 3a covalently modified the C128 site, and then regulated the N125-S124-S123 allosteric pathway of FBPase in mechanism. In summary, 3a has the potential to be a novel FBPase inhibitor for T2D therapy. (C) 2020 Elsevier Masson SAS. All rights reserved.