bis(1,2,3,4-tetrahydroisoquinolin-2-ylthiocarbonyl) disulfide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: bis(1,2,3,4-tetrahydroisoquinolin-2-ylthiocarbonyl) disulfide
• 英文别名: bis(3,4-dihydroisoquinoline-2(1H)-yl-thiocarbonyl)disulfide；3,4-dihydroisoquinoline-2(1H)-carbothioic dithioperoxyanhydride；bis-(3,4-dihydro-1H-isoquinoline-2-thiocarbonyl)-disulfane；Bis-(3,4-dihydro-1H-isochinolin-2-thiocarbonyl)-disulfan；3,4-dihydro-1H-isoquinoline-2-carbothioylsulfanyl 3,4-dihydro-1H-isoquinoline-2-carbodithioate
• 化学式: C₂₀H₂₀N₂S₄
• 分子量: 416.656
• InChiKey: RXSZRGMRAQEECZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  121
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  吲哚 、 bis(1,2,3,4-tetrahydroisoquinolin-2-ylthiocarbonyl) disulfide 在 potassium tert-butylate 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以73%的产率得到indol-1-yl 3,4-dihydro-1H-isoquinoline-2-carbodithioate
  参考文献：
  名称：

  一种N-二硫代氨基甲酸酯吲哚类化合物的制 备方法

  摘要：

  本发明公开了一种N‑二硫代氨基甲酸酯吲哚类化合物的制备方法，包括：在DCE或甲苯溶剂中，用叔丁醇钾作碱，以吲哚类化合物与秋兰姆类化合物为底物，合成N‑二硫代氨基甲酸酯吲哚类化合物。本发明方法通过化学选择性的形成N‑S键首次合成了N‑二硫代氨基甲酸酯吲哚类化合物。本发明反应原料廉价易得，制备方法简单，用叔丁醇钾作碱，室温下反应，反应时间短，产率高，操作简单，适用于不同类型的N‑二硫代氨基甲酸酯吲哚类化合物的合成。本发明方法可用于合成一系列的N‑二硫代氨基甲酸酯吲哚类化合物，合成的产物不仅可作为中间化合物，用于进一步构筑复杂的活性化合物；同时该类化合物具有极大的药物活性潜力。

  公开号：

  CN109384702B
• 作为产物：
  描述：

  在 盐酸 、 sodium nitrite 作用下， 以 甲醇 、 水 为溶剂， 生成 bis(1,2,3,4-tetrahydroisoquinolin-2-ylthiocarbonyl) disulfide
  参考文献：
  名称：

  Bis(dialkylaminethiocarbonyl)disulfides as Potent and Selective Monoglyceride Lipase Inhibitors

  摘要：

  Monoglyceride lipase (MGL) inhibition may offer an approach in treating diseases in which higher 2-arachidonoyglycerol activity would be beneficial. We report here the synthesis and pharmacological evaluation of bis(dialkylaminethiocarbonyl)disulfide derivatives as irreversible MGL inhibitors. Inhibition occurs through interactions with MGL C208 and C242 residues, and these derivatives exhibit high inhibition selectivity over fatty acid amide hydrolase, another endocannabinoid-hydrolyzing enzyme.

  DOI：

  10.1021/jm901323s

文献信息

• Cerium ammonium nitrate-catalyzed aerobic oxidative coupling of dithiocarbamates: facile synthesis of thioureas and bis(aminothiocarbonyl)disulfides
  作者：Tian-Tian Li、Xiang-Hai Song、Mei-Shuang Wang、Ning Ma

  DOI：10.1039/c4ra04628e

  日期：——

  Diverse disubstituted and trisubstituted thioureas were synthesized by the condensation of dithiocarbamate TEA (or DABCO) salts and amines using cerium ammonium nitrate (CAN) as a catalyst in high yields at room temperature. It is a one-pot method and it is unnecessary to isolate isothiocyanates. This reaction probably took place through nucleophilic addition of amines to isothiocyanates, which were generated by oxidative coupling of dithiocarbamates and the following decomposition of bis(aminothiocarbonyl)disulfides. When secondary amines and CS2 served as the reactants, bis(aminothiocarbonyl)disulfides were obtained via tandem nucleophilic addition/oxidative coupling reactions in moderate to excellent yields. In all the coupling reactions, the oxidant was air and CAN possibly acted as an SET catalyst.

  多种二取代和三取代硫脲通过二硫代氨基甲酸TEA（或DABCO）盐与胺在室温下使用硝酸铈铵（CAN）作为催化剂进行缩合反应，以高产率合成。这是一种一步法，无需分离异硫氰酸酯。该反应可能涉及胺对异硫氰酸酯的亲核加成，异硫氰酸酯是由二硫代氨基甲酸盐的氧化偶联以及随后双(氨基硫羰基)二硫化物的分解产生的。当使用二级胺和CS2作为反应物时，通过串联的亲核加成/氧化偶联反应，以中等至优异的产率获得了双(氨基硫羰基)二硫化物。在所有偶联反应中，氧化剂为空气，CAN可能作为单电子转移催化剂发挥作用。
• 二硫化秋兰姆类化合物及合成工艺
  申请人：科迈化工股份有限公司

  公开号：CN109400510A

  公开（公告）日：2019-03-01

  本发明属于橡胶助剂领域，具体是涉及一种二硫化秋兰姆类化合物及合成工艺，包括下述步骤1)：仲胺与碱液混合后，滴加二硫化碳，其中，仲胺、碱液、和二硫化碳的摩尔比为1：(1‑2)：(1‑2)，反应温度为30‑60℃,得到二硫代甲酸钠中间体；2)，将步骤1)得到的二硫代甲酸钠中间体、二甲亚砜以及分散剂混合搅拌后，滴加强酸催化剂，反应温度为30‑80℃；其中，二硫代甲酸钠中间体：二甲亚砜：强酸催化剂的摩尔比为2：(1‑1.8)：(2‑4)，其中催化剂的摩尔量以氢离子计。生成目标产物。该反应产品收率可到95％以上产物经HPLC测试纯度可到96％。
• Metal-Free Thiocarbamation of Quinolinones: Direct Access to 3,4-Difunctionalized Quinolines and Quinolinonyl Thiocarbamates at Room Temperature
  作者：Linkun Ying、Yao Chen、Xiangrui Song、Zengqiang Song

  DOI：10.1021/acs.joc.3c01504

  日期：2023.10.6

  group at the C4-position, and quinolinonyl thiocarbamates from quinolinones, tetraalkylthiuram disulfides, and hypervalent iodine(III) reagents has been developed via thiocarbamation of quinolinones at room temperature. The present method features mild reaction conditions, good tolerance with diverse functional groups, and a wide substrate scope, providing the desired products in good yields. Furthermore

  开发了一种新颖且实用的方法，用于从喹啉酮、二硫化四烷基秋兰姆和高价碘 (III) 试剂制备在 C3 位上带有硫代氨基甲酸酯基团和在 C4 位上带有酰氧基基团的双官能化喹啉和喹啉酮基硫代氨基甲酸酯。在室温下通过喹啉酮的硫代氨基甲酸酯化。该方法反应条件温和，对多种官能团具有良好的耐受性，底物范围广，能够以良好的产率提供所需的产物。此外，这种转化很容易扩大规模，并且所需的产物可以很容易地转化为杂环硫醇。最重要的是，该方案允许生物活性化合物的后期硫代氨基甲酸酯化。机理研究表明，自由基可能参与了这种转变，水可能是硫代氨基甲酸盐的氧源，双官能化喹啉可能是通过源自高价碘（III）试剂的羧酸阴离子的亲核攻击形成的。
• 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.
• Reduced Graphene Oxide as Recyclable Catalyst for Synthesis of Bis(aminothiocarbonyl)disulfides from Secondary Amines and Carbon Disulfide
  作者：Meishuang Wang、Xianghai Song、Ning Ma

  DOI：10.1007/s10562-014-1257-x

  日期：2014.7

  The reaction of secondary amines with CS2 under mild conditions using reduced graphene oxide (rGO) as a green catalyst was reported, which provided an efficient access to the one-pot synthesis of bis(aminothiocarbonyl)disulfides. The rGO can be recycled at least four times without any loss of catalytic activity. A plausible mechanism was proposed.