triethylamine thiocarbamate | 57381-11-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: triethylamine thiocarbamate
• 英文别名: N,N-diethylethanamine;(4-sulfamoylphenyl)carbamodithioic acid
• CAS: 57381-11-0
• 化学式: C₆H₁₅N*C₇H₈N₂O₂S₃
• 分子量: 349.543
• InChiKey: VNNJMPJLPASSAB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.31
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  117
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  triethylamine thiocarbamate 在 碘 、 碳酸氢钠 作用下， 以 乙醇 、 水 、 乙酸乙酯 为溶剂， 生成 N-[4-(aminosulfonyl)phenyl]-2-(4-fluorobenzoyl)-1-hydrazinecarbothioamide
  参考文献：
  名称：

  Benzenesulfonamide bearing 1,2,4-triazole scaffolds as potent inhibitors of tumor associated carbonic anhydrase isoforms hCA IX and hCA XII

  摘要：

  Three series of novel heterocyclic compounds (3a-3g, 4a-4g and 5a-5g) containing benzenesulfonamide moiety and incorporating a 1,2,4-triazole ring, have been synthesized and investigated as inhibitors against four isomers of the alpha-class carbonic anhydrases (CAs, EC 4.2.1.1), comprising hCAs I and II (cytosolic, ubiquitous isozymes) and hCAs IX and XII (transmembrane, tumor associated isozymes). Against the human isozymes hCA I and II, compounds of two series (3a-3g and 4a-4g) showed K-i values in the range of 84-868 nM and 5.6-390 nM, respectively whereas compounds of series 5a-5g were found to be poor inhibitors (K-i values exceeding 10,000 nM in some cases). Against hCA IX and XII, all the tested compounds exhibited excellent to moderate inhibitory potential with K-i values in the range of 2.8-431 nM and 1.3-63 nM, respectively. Compounds 3d, 3f and 4f exhibited excellent inhibitory potential against all of the four isozymes hCA I, II, IX and XII, even better than the standard drug acetazolamide (AZA) whereas compound of the series 5a-5g were comparatively less potent but more selective towards hCA IX and XII. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.01.055
• 作为产物：
  描述：

  二硫化碳 、 磺胺 、 三乙胺 以 甲醇 为溶剂， 生成 triethylamine thiocarbamate
  参考文献：
  名称：

  含有 1,2,4-三唑的新型苯磺酰胺作为有效的抗微生物和抗氧化剂

  摘要：

  合成了一系列包含 30 种带有 1,2,4-三唑1a – 1h、2a – 2h、3a – 3h、4b – 4f和4h的新型苯磺酰胺，并作为抗微生物和抗氧化剂进行了研究。所有测试的化合物对测试的革兰氏阳性（金黄色葡萄球菌 ATCC 6538P、李斯特菌 MTCC 657和蜡样芽孢杆菌 ATCC 11770）和革兰氏阴性（铜绿假单胞菌 ATCC 15442、大肠杆菌 MTCC 143、伤寒沙门氏菌 MTCC ）均表现出中度至极好的抑制潜力733,福氏志贺菌ATCC 9199) 最小抑菌浓度值范围为 3.12 至 12.5 µg/mL 的细菌菌株。化合物3d与参考药物相比，对所有测试的细菌和真菌菌株都是等效或更好的抑制剂。还发现所有测试的化合物对正常细胞都是安全的，对小鼠成纤维细胞系的细胞活力为 89.8-99.8%，对植物种子萌发是 100% 安全的。还使用 DPPH 方法筛选了最终化合物的抗

  DOI：

  10.1007/s00044-023-03024-y
• 作为试剂：
  描述：

  2-溴苯乙酮 在 triethylamine thiocarbamate 作用下， 以 1,4-二氧六环 为溶剂， 反应 12.0h， 以60%的产率得到4-(4-phenyl-2-thioxothiazole-3-yl)benzenesulfonamide
  参考文献：
  名称：

  US2003/236289

  摘要：

  公开号：

文献信息

• Novel benzenesulfonamide‐bearing pyrazoles and 1,2,4‐thiadiazoles as selective carbonic anhydrase inhibitors
  作者：Rajiv Kumar、Amit Kumar、Sita Ram、Andrea Angeli、Alessandro Bonardi、Alessio Nocentini、Paola Gratteri、Claudiu T. Supuran、Pawan K. Sharma

  DOI：10.1002/ardp.202100241

  日期：2022.1

  tumor-associated isoforms IX and XII. Molecular modeling studies of some potent derivatives (8a, 8c, 10a, and 10c) were also performed against isoforms hCA I, II, and XII. Both the promising series of compounds were synthesized by using commercially available mtethyl ketones and sulfanilamide as the starting materials. Interestingly, this paper also reports a novel methodology for the synthesis of amino-1,2,4-thiadiazoles

  合成了两个系列，包括 20 种带有硫脲基连接的吡唑8和氨基-1,2,4-噻二唑10的新型苯磺酰胺，并作为人碳酸酐酶 (hCA) 抑制剂针对亚型 I 和 II 以及肿瘤相关亚型 IX 和十二．还针对亚型 hCA I、II 和 XII 进行了一些有效衍生物（ 8a 、 8c 、 10a和10c ）的分子模型研究。这两个有前景的系列化合物都是使用市售的甲基酮和磺胺作为起始原料合成的。有趣的是，本文还报道了一种使用3-氨基异恶唑和4-异硫氰酸苯磺酰胺作为反应物合成氨基-1,2,4-噻二唑10的新方法。所有新合成的化合物的活性特征表明，与硫脲基连接的吡唑8相比，氨基连接的 1,2,4-噻二唑10是胞质异构体 hCA I 更好的抑制剂。此外，hCA II 几乎被所有新合成的磺酰胺类药物强烈抑制，而与标准药物乙酰唑胺相比，所有化合物作为 hCA IX 和 XII 抑制剂的效果较差。然而，就选择性而言，化合物8e被发现是hCA
• Novel <i>self</i>-condensation of ammonium dithiocarbamates leading to symmetrical substituted thioureas
  作者：Şevket Hakan Üngören、Fatih Sırça

  DOI：10.1080/10426507.2016.1223075

  日期：2017.1.2

  GRAPHICAL ABSTRACT ABSTRACT For the first time, the formation of symmetrical substituted thiourea analogues generated by the self-condensation of trialkylammoniumdithiocarbamates is reported. The reactions occurred under mild conditions. The method allows the use of amines possessing a weak nucleophilic feature in good yields. The highlight of the study is a novel self-condensation mechanism based

  图形摘要摘要首次报道了由二硫代氨基甲酸三烷基铵自缩合生成的对称取代硫脲类似物的形成。反应在温和条件下发生。该方法允许以良好的产率使用具有弱亲核特征的胺。该研究的亮点是一种基于二硫代氨基甲酸酯作为有机化学基本化合物的新型自缩合机制。
• [EN] 2-THIOXOTHIAZOLE DERIVATIVE, METHOD FOR PREPARING THE SAME, AND PHARMACEUTICAL COMPOSITION CONTAINING THE SAME<br/>[FR] DERIVE DE 2-THIOXOTHIAZOLE, PROCEDE DE PREPARATION DE CE DERIVE ET COMPOSITION PHARMACEUTIQUE CONTENANT CE DERIVE
  申请人：CJ CORP

  公开号：WO2004000822A1

  公开（公告）日：2003-12-31

  A 2-thioxothiazole derivative of formula 1 or a non-toxic salt thereof, a preparation method thereof, and a pharmaceutical composition containing the derivative or the salt as an active ingredient are provided.

  本发明提供了一种公式1的2-硫代噻唑衍生物或其无毒盐，其制备方法以及含有该衍生物或盐作为活性成分的药物组合物。
• Potent inhibitors of tumor associated carbonic anhydrases endowed with cathepsin B inhibition
  作者：Amit Kumar、Priyanka Arya、Vikas Sharma、Simone Giovannuzzi、Neera Raghav、Claudiu T. Supuran、Pawan K. Sharma

  DOI：10.1002/ardp.202300349

  日期：2023.11

  Twenty‐one novel extended analogs of acetazolamide were synthesized and screened in vitro for their inhibition efficacy against human carbonic anhydrase (hCA) isoforms I, II, IX, XII, and cathepsin B. The majority of the compounds were found to be effective inhibitors of tumor‐associated hCA IX and XII, and poor inhibitors of cytosolic hCA I. Despite the strong to moderate inhibition potential possessed by these compounds toward another cytosolic isoform hCA II, some of them demonstrated better potency against hCA IX and/or XII isoforms as compared to hCA II. Four compounds (11f, 11g, 12c, and 12g) effectively inhibited hCA IX and/or XII isoforms with considerable selectivity over the off‐targets hCA I and II. Interestingly, five compounds, including 11f, 11g, 12c, 12d, and 12g, inhibited hCA IX even better than the clinically used acetazolamide. Some of the novel synthesized compounds exhibited higher anti‐cathepsin B potential than acetazolamide, with % inhibition of around 50%, at a concentration of 10⁻⁷ M. Further, two compounds (12g and 12c) that showed effective and selective inhibition activity profiles against hCA IX and XII were additionally found to be effective inhibitors of cathepsin B.

  摘要 合成了 21 种新型乙酰唑胺扩展类似物，并在体外筛选了它们对人碳酸酐酶（hCA）同工酶 I、II、IX、XII 和 cathepsin B 的抑制效果。尽管这些化合物对另一种细胞膜异构体 hCA II 具有较强至中等程度的抑制潜力，但与 hCA II 相比，其中一些化合物对 hCA IX 和/或 XII 异构体具有更强的抑制作用。四种化合物（11f、11g、12c 和 12g）有效抑制了 hCA IX 和/或 XII 同工酶，其选择性远远高于非靶标 hCA I 和 II。有趣的是，包括 11f、11g、12c、12d 和 12g 在内的五个化合物对 hCA IX 的抑制作用甚至优于临床常用的乙酰唑胺。与乙酰唑胺相比，一些新合成的化合物具有更高的抗胰蛋白酶 B 的潜力，在 10-7 M 浓度下，抑制率约为 50%。此外，还发现两种化合物（12g 和 12c）对 hCA IX 和 XII 具有有效的选择性抑制活性，也是有效的钙蛋白 B 抑制剂。
• Benzenesulfonamide bearing 1,2,4-triazole scaffolds as potent inhibitors of tumor associated carbonic anhydrase isoforms hCA IX and hCA XII
  作者：SitaRam、Gulsah Celik、Poonam Khloya、Daniela Vullo、Claudiu T. Supuran、Pawan K. Sharma

  DOI：10.1016/j.bmc.2014.01.055

  日期：2014.3

  Three series of novel heterocyclic compounds (3a-3g, 4a-4g and 5a-5g) containing benzenesulfonamide moiety and incorporating a 1,2,4-triazole ring, have been synthesized and investigated as inhibitors against four isomers of the alpha-class carbonic anhydrases (CAs, EC 4.2.1.1), comprising hCAs I and II (cytosolic, ubiquitous isozymes) and hCAs IX and XII (transmembrane, tumor associated isozymes). Against the human isozymes hCA I and II, compounds of two series (3a-3g and 4a-4g) showed K-i values in the range of 84-868 nM and 5.6-390 nM, respectively whereas compounds of series 5a-5g were found to be poor inhibitors (K-i values exceeding 10,000 nM in some cases). Against hCA IX and XII, all the tested compounds exhibited excellent to moderate inhibitory potential with K-i values in the range of 2.8-431 nM and 1.3-63 nM, respectively. Compounds 3d, 3f and 4f exhibited excellent inhibitory potential against all of the four isozymes hCA I, II, IX and XII, even better than the standard drug acetazolamide (AZA) whereas compound of the series 5a-5g were comparatively less potent but more selective towards hCA IX and XII. (C) 2014 Elsevier Ltd. All rights reserved.