N-methyl-2-(4-nitrobenzylidene)hydrazinecarbothioamide | 51146-60-2

• 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-methyl-2-(4-nitrobenzylidene)hydrazinecarbothioamide
• 英文别名: N(4)-methyl-4-nitrobenzaldehyde thiosemicarbazone；N4-methyl-4-nitrobenzaldehyde thiosemicarbazone；4-nitrobenzaldehyde N4-methylthiosemicarbazone；4-nitrobenzaldehyde-4-methylthiosemicarbazone；4-nitro-benzaldehyde 4-methyl-thiosemicarbazone；H4NO2Fo4M；1-Methyl-3-[(4-nitrophenyl)methylideneamino]thiourea
• CAS: 51146-60-2
• 化学式: C₉H₁₀N₄O₂S
• 分子量: 238.27
• InChiKey: SVOLUGVHMCTSGL-UHFFFAOYSA-N

物化性质

• 熔点：
  230-232 °C
• 沸点：
  379.7±44.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  114
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-methyl-2-(4-nitrobenzylidene)hydrazinecarbothioamide 在 三氯化铁 作用下， 生成 methyl-[(4-nitro-phenyl)-[1,3,4]thiadiazol-2-yl]-amine
  参考文献：
  名称：

  De; Roy-Choudhury, Journal of the Indian Chemical Society, 1928, vol. 5, p. 272

  摘要：

  DOI：
• 作为产物：
  描述：

  对硝基苯甲醛 、 4-甲基氨基硫脲 以 乙醇 为溶剂， 反应 0.5h， 以57%的产率得到N-methyl-2-(4-nitrobenzylidene)hydrazinecarbothioamide
  参考文献：
  名称：

  2‐Hydrazono‐2,3‐dihydro‐1,3-噻唑类化合物意外环扩大为1,3,4‐噻二嗪类化合物

  摘要：

  硫代氨基脲与α-溴乙酰苯的环化可导致形成1,3,4-噻二嗪异构体和两种不同的噻唑。我们研究了使用4-甲基和4-乙基硫代氨基脲作为双亲核基石。在这种情况下，我们观察到了前所未有的2-肼基-2-2,3-二氢噻唑重排为1,3,4-噻二嗪的过程。1,3,4-噻二嗪对噻唑的环收缩很常见，而环的扩张则是新的。反应过程取决于底物的取代方式。

  DOI：

  10.1002/hlca.201300077

文献信息

• Unexpected Ring Enlargement of 2-Hydrazono-2,3-dihydro-1,3-thiazoles to 1,3,4-Thiadiazines
  作者：Wolf-Diethard Pfeiffer、Klaus-Dieter Ahlers、Ashot S. Saghyan、Alexander Villinger、Peter Langer

  DOI：10.1002/hlca.201300077

  日期：2014.1

  α‐bromoacetophenone can result in the formation of isomeric 1,3,4‐thiadiazines and two different thiazoles. We studied the use of 4‐methyl‐ and 4‐ethylthiosemicarbazide as dinucleophilic building blocks. In this context, we observed an unprecedented rearrangement of a 2‐hydrazono‐2,3‐dihydrothiazole to a 1,3,4‐thiadiazine. While ring contractions of 1,3,4‐thiadiazines to thiazoles are quite common, ring enlargements

  硫代氨基脲与α-溴乙酰苯的环化可导致形成1,3,4-噻二嗪异构体和两种不同的噻唑。我们研究了使用4-甲基和4-乙基硫代氨基脲作为双亲核基石。在这种情况下，我们观察到了前所未有的2-肼基-2-2,3-二氢噻唑重排为1,3,4-噻二嗪的过程。1,3,4-噻二嗪对噻唑的环收缩很常见，而环的扩张则是新的。反应过程取决于底物的取代方式。
• Cyclocondensations of Substituted Thiosemicarbazides with 2-Bromo- 1,2-diphenylethan-1-one
  作者：Wolf-Diethard Pfeiffer、Helmut Gille、Ehrenfried Bulka、Ashot Saghyan、Peter Langer

  DOI：10.5560/znb.2013-3036

  日期：2013.7.1

  The cyclocondensation of 4-methylthiosemicarbazide with 2-bromo-1,2-diphenylethan-1-one in ethanol afforded isomeric 2-methylamino-5,6-diphenyl-6H-3,4-thiadiazine and 2-hydrazono-3- methyl-4,5-diphenyl-2,3-dihydro-1,3-thiazole. A pyrazole was obtained by cyclocondensation and subsequent desulfurization of the thiadiazine when the reaction was carried out in concentrated hydrochloric acid. A chemical proof of the structures has been provided. The product distribution of the cyclizations strongly depends on the substitution pattern of the starting materials, and the cyclizations of methylthiosemicarbazide with 2-bromo-1,2-diphenylethan-1-one behaved considerably different from that of the analogous reactions of α-bromoacetophenone.

  在乙醇中，4-甲基硫代氨基脲与 2-溴-1,2-二苯基乙-1-酮发生环缩合反应，得到异构的 2-甲基氨基-5,6-二苯基-6H-3,4-噻二嗪和 2-酰肼基-3-甲基-4,5-二苯基-2,3-二氢-1,3-噻唑。当反应在浓盐酸中进行时，噻二嗪通过环缩合和随后的脱硫反应得到了吡唑。已提供了这些结构的化学证明。环化反应的产物分布在很大程度上取决于起始原料的取代模式，甲基硫代氨基甲酰与 2-溴-1,2-二苯基乙烷-1-酮的环化反应与 α-溴苯乙酮的类似反应有很大不同。
• Theoretical, antioxidant, antidiabetic and <i>in silico</i> molecular docking and pharmacokinetics studies of heteroleptic oxovanadium(IV) complexes of thiosemicarbazone-based ligands and diclofenac
  作者：Sumeer Ahmed、Ummer Muhammed Rafi、Raju Senthil Kumar、Ajmal Rashid Bhat、Malika Berredjem、Vidya Niranjan、Lavanya C.、Aziz Kalilur Rahiman

  DOI：10.1080/07391102.2023.2246565

  日期：——

  A series of new heteroleptic oxovanadium(IV) complexes with the general formula [VOL1–6(Dcf)] (1–6), where L1−6 = thiosemicarbazone (TSC)-based ligands and Dcf = diclofenac have been synthesized an...

  一系列新型杂配氧钒 (IV) 配合物的通式为 [VOL1–6(Dcf)] (1–6)，其中 L1−6 = 缩氨基硫脲 (TSC) 配体，Dcf = 双氯芬酸已被合成。 。
• Bulka,E. et al., Chemische Berichte, 1965, vol. 98, p. 259 - 273
  作者：Bulka,E. et al.

  DOI：——

  日期：——
• Coordination of nitro-thiosemicarbazones to ruthenium(II) as a strategy for anti-trypanosomal activity improvement
  作者：Claudia Rodrigues、Alzir A. Batista、Javier Ellena、Eduardo E. Castellano、Diego Benítez、Hugo Cerecetto、Mercedes González、Letícia R. Teixeira、Heloisa Beraldo

  DOI：10.1016/j.ejmech.2010.03.005

  日期：2010.7

  Complexes [RuCl(H4NO(2)Fo4M)(bipy)(dppb)]PF6 (1), [RuCl(H4NO(2)Fo4M)(Mebipy)(dppb)]PF6 (2), [RuCl(H4NO(2)Fo4M)(phen)(dppb)]PF6 (3), [RuCl(H4NO(2)Ac4M)(bipy)(dppb)]PF6 (4), [RuCl(H4NO(2)Ac4M)(Mebipy)(dppb)]PF6 (5) and [RuCl(H4NO(2)Ac4M)(phen)(dppb)]PF6 (6) with N-4-methyl-4-nitrobenzalde hyde thiosemicarbazone (H4NO(2)Fo4M) and N-4-methyl-4-nitroacetophenone thiosemicarbazone (H4NO(2) Ac4M) were obtained from [RuCl2(bipy)(dppb)], [RuCl2(Mebipy)(dppb)], and [RuCl2(phen)(dppb)], (dppb = 1,4-bis(diphenylphospine)butane; bipy = 2,2'-bipyridine: Mebipy = 4,4'-dimethyl-2,2'-bipyridine: phen = 1,10-phenanthroline). In all cases the thiosemicarbazone is attached to the metal center through the sulfur atom.Complexes (1-6), together with the corresponding ligands and the Ru precursors were evaluated for their ability to in vitro suppress the growth of Trypanosoma cruzi. All complexes were more active than their corresponding ligands and precursors. Complexes (1-3) and (5) revealed to be the most active among all studied compounds with ID50 = 0.6-0.8 mu M.In all cases the association of the thiosemicarbazone with ruthenium, dppb and bipyridine or phenanthroline in one same complex proved to be an excellent strategy for activity improvement. (C) 2010 Elsevier Masson SAS. All rights reserved.