2-硫代-1,2-二氢-3-吡啶甲酰肼 | 100367-73-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 2-硫代-1,2-二氢-3-吡啶甲酰肼
• 英文名称: 2-mercaptonicotinohydrazide
• 英文别名: 2-mercapto-nicotinic acid hydrazide；2-Mercapto-nicotinsaeure-hydrazid；2-Sulfanylidene-1,2-dihydropyridine-3-carbohydrazide；2-sulfanylidene-1H-pyridine-3-carbohydrazide
• CAS: 100367-73-5
• 化学式: C₆H₇N₃OS
• mdl: MFCD18833670
• 分子量: 169.207
• InChiKey: CCXSUYUCCHUHMP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  99.2
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-硫代-1,2-二氢-3-吡啶甲酰肼 在 hydrazine hydrate 、 potassium carbonate 、 potassium hydroxide 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 3-(14-chloro-8-thia-2,3,5,6,18-pentazatetracyclo[8.8.0.03,7.012,17]octadeca-1(10),4,6,11,13,15,17-heptaen-4-yl)-1H-pyridine-2-thione
  参考文献：
  名称：

  Triazolothiadizepinylquinolines as potential MetAP-2 and NMT inhibitors: Microwave-assisted synthesis, pharmacological evaluation and molecular docking studies

  摘要：

  The enzymes MetAP-2 and NMT play a crucial role in the process of myristoylation of oncoproteins which is deregulated in many types of cancers. Execution of both these enzymes is considered as strategy for the intervention of various cancers and relative fungal infections, and hence the discovery of novel MetAP-2 and NMT inhibitors necessitate their high relevancy. In this investigation, we have synthesized a series of novel seven-membered triazolothiadiazepinyl quinolines 10(a-m) distinctively under microwave irradiation technique and identified as selective MetAP-2 and NMT inhibitors. Amongst the functionalized derivatives when evaluated for the in vitro antifungal assay, compounds 10b, 10c, 10e and 10f were considered promising due to notable inhibitory effects (MIC = 0.2 mg/mL) on Aspergillus fumigatus. Screening of the anticancer activity against NCI-60 Human tumor cell lines portrayed that conjugates 10b, 10c, 10e and 10f were found to be moderately effective against the Renal Cancer cell line UO-31. The data acquired from biological studies was further validated by molecular docking studies and p harmaco kinetic evaluation. (C) 2019 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2019.127445
• 作为产物：
  描述：

  2-巯基烟酸 在 对甲苯磺酸 、 一水合肼 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 13.0h， 生成 2-硫代-1,2-二氢-3-吡啶甲酰肼
  参考文献：
  名称：

  2-（（3,5-二叔丁基-4-羟基苄基）硫代）烟酸酯酰化中C–S键的意外断裂：动力学和计算方法的合成和机理研究

  摘要：

  由2-巯基烟酸和2，6-二叔丁基-4-羟基-苄基醇成功合成了2-（（（3,5-二叔丁基-4-羟基苄基）硫代）甲基烟酸酯。酯的酰肼化是制备酰基酰肼，2-（3,5-二叔丁基-4-羟基-苄基硫烷基）-烟酸酰肼的常规方法。但是，尝试通过水合肼在醇溶液中合成原料并没有得到预期的产物。观察到意外的C–S键断裂，产生了两种化合物，即2-thioxo-1,2-二氢吡啶-3-羧酸酰肼和2,6-二叔丁基-4-肼基甲基苯酚。为了提出一个合理的机制，进行了动力学和计算的DFT研究。

  DOI：

  10.1016/j.tet.2015.10.077

文献信息

• Unexpected cleavage of C–S bond in the hydrazination of 2-((3,5-di- tert -butyl-4-hydroxybenzyl)thio) nicotinate: synthesis and mechanistic studies by kinetic and computational approaches
  作者：Nurdiana Nordin、Azhar Ariffin、Mohammad Noh Daud、Yoke-Leng Sim

  DOI：10.1016/j.tet.2015.10.077

  日期：2016.2

  material in alcoholic solution by hydrazine hydrate did not lead to the expected products. Unexpected C–S bond cleavage was observed that produced two compounds, 2-thioxo-1,2-dihydro-pyridine-3-carboxylic acid hydrazide, and 2,6-di-tert-butyl-4-hydrazinomethylphenol. A kinetic and a computational DFT studies were carried out in order to propose a rational mechanism.

  由2-巯基烟酸和2，6-二叔丁基-4-羟基-苄基醇成功合成了2-（（（3,5-二叔丁基-4-羟基苄基）硫代）甲基烟酸酯。酯的酰肼化是制备酰基酰肼，2-（3,5-二叔丁基-4-羟基-苄基硫烷基）-烟酸酰肼的常规方法。但是，尝试通过水合肼在醇溶液中合成原料并没有得到预期的产物。观察到意外的C–S键断裂，产生了两种化合物，即2-thioxo-1,2-二氢吡啶-3-羧酸酰肼和2,6-二叔丁基-4-肼基甲基苯酚。为了提出一个合理的机制，进行了动力学和计算的DFT研究。
• Acetato-bridged dinuclear lanthanide complexes with single molecule magnet behaviour for the Dy₂ species
  作者：Haixia Zhang、Shuang-Yan Lin、Shufang Xue、Chao Wang、Jinkui Tang

  DOI：10.1039/c3dt53366b

  日期：——

  lanthanide complexes with formula [Ln2L2(OAc)4(MeOH)a(H2O)b]·cMeOH·dH2O (a = 2, b = 0, c = 2, d = 0, Ln = Sm (1), Gd (2), Dy (3); a = 0, b = 2, c = 4, d = 2, Ln = Tm (4)) and [Yb2L2(OAc)4(MeOH)2]·[Yb2L2(OAc)4(H2O)2]·2H2O (5) (HL = (E)-N′-(2-hydroxybenzylidene)-2-mercaptonicotinohydrazide), have been synthesized and their crystal structures and magnetic properties are reported. All five complexes are

  五个具有式[Ln 2 L 2（OAc）4（MeOH）a（H 2 O）b ]· c MeOH· d H 2 O的双核镧系元素络合物（a = 2，b = 0，c = 2，d = 0 ，Ln = Sm（1），Gd（2），Dy（3）; a = 0，b = 2，c = 4，d = 2，Ln = Tm（4））和[Yb 2 L 2（OAc）4（甲醇）2合成了]·[Yb 2 L 2（OAc）4（H 2 O）2 ]·2H 2 O（5）（HL =（E）-N '-（2-羟基亚苄基）-2-巯基二十二酰肼）报告了它们的晶体结构和磁性。所有五个配合物是中心对称的，示出了每个复数下使用两个镧系元素离子的类似的双核芯在η桥接由乙酸酯基团1：η 2：μ 2模式。乙酸酯基团的各种配位模式导致Ln离子具有两种配位几何结构，其中配位体1-4和Yb2在配合物中。在图5中，Y 5与单封顶正方形反棱镜几何结构呈九坐标，而在配合物5的另一部分中的Yb
• HYDRAZINE DERIVATIVES. II. ortho-MERCAPTOPYRIDINECARBOHYDRAZIDES
  作者：LEON KATZ、WILLIAM SCHROEDER、MURRAY COHEN

  DOI：10.1021/jo01370a002

  日期：1954.5
• Production of 4-mercaptonicotinic acid and intermediate therefor
  申请人：SCHENLEY IND INC

  公开号：US02824876A1

  公开（公告）日：1958-02-25
• Triazolothiadizepinylquinolines as potential MetAP-2 and NMT inhibitors: Microwave-assisted synthesis, pharmacological evaluation and molecular docking studies
  作者：Saba Kauser J. Shaikh、Ravindra R. Kamble、Praveen K. Bayannavar、Shilpa M. Somagond、Shrinivas D. Joshi

  DOI：10.1016/j.molstruc.2019.127445

  日期：2020.3

  The enzymes MetAP-2 and NMT play a crucial role in the process of myristoylation of oncoproteins which is deregulated in many types of cancers. Execution of both these enzymes is considered as strategy for the intervention of various cancers and relative fungal infections, and hence the discovery of novel MetAP-2 and NMT inhibitors necessitate their high relevancy. In this investigation, we have synthesized a series of novel seven-membered triazolothiadiazepinyl quinolines 10(a-m) distinctively under microwave irradiation technique and identified as selective MetAP-2 and NMT inhibitors. Amongst the functionalized derivatives when evaluated for the in vitro antifungal assay, compounds 10b, 10c, 10e and 10f were considered promising due to notable inhibitory effects (MIC = 0.2 mg/mL) on Aspergillus fumigatus. Screening of the anticancer activity against NCI-60 Human tumor cell lines portrayed that conjugates 10b, 10c, 10e and 10f were found to be moderately effective against the Renal Cancer cell line UO-31. The data acquired from biological studies was further validated by molecular docking studies and p harmaco kinetic evaluation. (C) 2019 Elsevier B.V. All rights reserved.