N‐(4‐sulfamoylphenyl)hydrazinecarbothioamide | 95856-64-7

• 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: N‐(4‐sulfamoylphenyl)hydrazinecarbothioamide
• 英文别名: 4-Hydrazinothiocarbonylamino-benzenesulfonamide；1-amino-3-(4-sulfamoylphenyl)thiourea
• CAS: 95856-64-7
• 化学式: C₇H₁₀N₄O₂S₂
• 分子量: 246.314
• InChiKey: OCAOKPDFGVWYGC-UHFFFAOYSA-N

物化性质

• 熔点：
  185 °C
• 沸点：
  462.0±55.0 °C(Predicted)
• 密度：
  1.585±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  151
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N‐(4‐sulfamoylphenyl)hydrazinecarbothioamide 在 盐酸 、 sodium nitrite 作用下， 生成 M-(1,2,3,4-噻三唑-5-基氨基)苯磺酰胺
  参考文献：
  名称：

  Dubenko,R.G. et al., Journal of general chemistry of the USSR, 1963, vol. 33, p. 266 - 268

  摘要：

  DOI：
• 作为产物：
  描述：

  (4-sulfamoyl-phenyl)-dithiocarbamic acid ; potassium-salt 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 N‐(4‐sulfamoylphenyl)hydrazinecarbothioamide
  参考文献：
  名称：

  5-Nitrofuran-2-yl derivatives: Synthesis and inhibitory activities against growing and dormant mycobacterium species

  摘要：

  Eighteen 5-nitrofuran-2-yl derivatives were prepared by reacting 5-nitro-2-furfural with various (sub)phenyl/pyridyl thiosemicarbazide using microwave irradiation. The compounds were tested for their in vitro activity against tubercular and various non-tubercular mycobacterium species in log-phase and 6-week-starved cultures. Compound N-(3,5-dibromopyridin-2-yl)-2-((5-nitrofuran-2-yl) methylene) hydrazinecarbothioamide (4r) was found to be the most potent compound (MIC: 0.22 mu M) and was 3 times more active than standard isoniazid (INH) and equally active as rifampicin (RIF) in log-phase culture of Mycobacterium tuberculosis H37Rv. In starved M. tuberculosis H37Rv, 4r inhibited with MIC of 13.9 mu M and was found to be 50 times more active than INH and slightly more active than RIF. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.12.088

文献信息

• Synthesis and anticonvulsant and neurotoxicity evaluation of N4-phthalimido phenyl (thio) semicarbazides
  作者：P Yogeeswari、D Sriram、V Saraswat、J.Vaigunda Ragavendran、M.Mohan Kumar、S Murugesan、R Thirumurugan、J.P Stables

  DOI：10.1016/j.ejps.2003.08.002

  日期：2003.11

  The phenyl (thio) semicarbazide derivatives of phthalimido pharmacophore were synthesized and evaluated for their anticonvulsant and neurotoxic properties. Initial anticonvulsant screening was performed using intraperitoneal (i.p.), maximal electroshock-induced seizure (MES), subcutaneous pentylenetetrazole (scPTZ) and subcutaneous strychnine (sc STY)-induced seizure threshold tests in mice. Compound

  合成了邻苯二甲酰亚胺药效基团的苯基（硫代）氨基脲衍生物，并对其抗惊厥和神经毒性特性进行了评估。在小鼠中使用腹膜内（ip），最大电击诱发的癫痫发作（MES），皮下戊烯四唑（scPTZ）和皮下士的宁（sc STY）诱发的癫痫发作阈值测试进行了初始抗惊厥筛选。化合物2c在所有三个屏幕中均提供了保护。除1d，2a和2d外的化合物在300 mg / kg以下均无神经毒性。发现化合物1a，1b，2c，2d，2g和2i具有口服MES活性。该化合物表现出中枢神经系统抑制和行为绝望的副作用，比常规的抗癫痫药要小。
• [EN] USE OF DERIVATIVES OF 2, 4-DIHYDRO-[1,2,4]TRIAZOLE-3-THIONE AS INHIBITORS O FTEH ENZYME MYELOPEROXIDASE (MPO)<br/>[FR] UTILISATION DE DERIVES DE 2, 4-DIHYDRO-[1,2,4]TRIAZOLE-3-THIONES COMME INHIBITEURS DE L'ENZYME MYELOPEROXYDASE (MPO)
  申请人：ASTRAZENECA AB

  公开号：WO2004096781A1

  公开（公告）日：2004-11-11

  There is disclosed the use of a compound of formula (I) wherein X, Y, W and Q are as defined in the specification, and pharmaceutically acceptable salts thereof, in the manufacture of a medicament, for the treatment or prophylaxis of diseases or conditions in which inhibition of the enzyme myeloperoxidase (MPO) is beneficial. Certain novel compounds of formula (I) and pharmaceutically acceptable salts thereof are disclosed, together with processes for their preparation. The compounds of formulae (I) are MPO inhibitors and are thereby particularly useful in the treatment or prophylaxis of neuroinflammatory disorders.

  揭示了使用公式(I)中X、Y、W和Q如规范中定义的化合物及其药用盐，在制造药物中用于治疗或预防对髓过氧化物酶（MPO）抑制有益的疾病或症状。公开了某些公式(I)的新化合物及其药用盐，以及它们的制备方法。公式(I)的化合物是MPO抑制剂，因此在治疗或预防神经炎症性疾病中特别有用。
• Use of derivatives of 2, 4-dihydro-[1,2,4] triazole-3-thione as inhibitors of the enzyme myeloperoxidase (mpo)
  申请人：Svensson Mats

  公开号：US20070093483A1

  公开（公告）日：2007-04-26

  There is disclosed the use of a compound of formula (I) wherein X, Y, W and Q are as defined in the specification, and pharmaceutically acceptable salts thereof, in the manufacture of a medicament, for the treatment or prophylaxis of diseases or conditions in which inhibition of the enzyme myeloperoxidase (MPO) is beneficial. Certain novel compounds of formula (I) and pharmaceutically acceptable salts thereof are disclosed, together with processes for their preparation. The compounds of formulae (I) are MPO inhibitors and are thereby particularly useful in the treatment or prophylaxis of neuroinflammatory disorders.

  本发明揭示了使用化合物(I)的使用，其中X、Y、W和Q如规范中所定义，以及其药学上可接受的盐，在制造药物方面，用于治疗或预防抑制髓过氧化物酶（MPO）酶有益的疾病或状况。揭示了某些新型化合物(I)及其药学上可接受的盐，以及其制备方法。化合物(I)的MPO抑制剂，因此特别适用于治疗或预防神经炎症性疾病。
• 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。
• DE852086
  申请人：——

  公开号：——

  公开（公告）日：——