N1-[4-(phenylsulfonyl)benzoyl]-N4-(4-trifluoromethoxyphenyl)-thiosemicarbazide | 1361970-40-2

• 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: N1-[4-(phenylsulfonyl)benzoyl]-N4-(4-trifluoromethoxyphenyl)-thiosemicarbazide
• 英文别名: 1-[[4-(Benzenesulfonyl)benzoyl]amino]-3-[4-(trifluoromethoxy)phenyl]thiourea
• CAS: 1361970-40-2
• 化学式: C₂₁H₁₆F₃N₃O₄S₂
• 分子量: 495.503
• InChiKey: CTXBSRNAIKDQAR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  137
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N1-[4-(phenylsulfonyl)benzoyl]-N4-(4-trifluoromethoxyphenyl)-thiosemicarbazide 在 sodium hydroxide 、 盐酸 作用下， 以 水 为溶剂， 反应 5.0h， 以63.5%的产率得到5-(4-(phenylsulfonyl)phenyl)-4-(4-trifluoromethoxyphenyl)-2H-1,2,4-triazol-3(4H)-thione
  参考文献：
  名称：

  New heterocyclic compounds from 1,2,4-triazole and 1,3,4-thiadiazole class bearing diphenylsulfone moieties. Synthesis, characterization and antimicrobial activity evaluation

  摘要：

  Some new 5-(4-(4-X-phenylsulfonyl)phenyl)-4-(R)-2H-1,2,4-triazol-3(4H)-thiones 4a,b; 5a,b and 5-(4-(4-X-phenylsulfonyl)phenyl)-N-(R)-1,3,4-thiadiazol-2-amines 6a,b; 7a,b were obtained by cyclization of new N-1-[4-(4-X-phenylsulfonyl)benzoyl]-N-4-(R)-thiosemicarbazides 2a,b; 3a,b (X = H, Br). The 1,2,4-triazoles were synthesized by intramolecular cyclization of acylthiosemicarbazides, in basic media. On the other hand, 1,3,4-thiadiazoles were obtained from same acylthiosemicarbazides, in acidic media. These new intermediates from thiosemicarbazide class were afforded by the reaction of 4-(4-X-phenylsulfonyl)benzoic acids hydrazides (X = H, Br) la,b with 4-trifluoromethoxyphenyl or 3,4,5-trimethoxyphenyl isothiocyanate. The newly synthesized compounds were characterized by IR, H-1 NMR, C-13 NMR, MS and elemental analysis. All the new compounds were screened for their antimicrobial activity against some bacteria (Staphylococcus aureus ATCC 25923, Bacillus cereus ATCC 13061, Escherichia coli ATCC 25922, Enterobacter cloacae ATCC 49141, Acinetobacter baumannii ATCC 19606 and Pseudomonas aeruginosa ATCC 27853) and yeasts (Candida albicans ATCC 90028 and Candida parapsilosis ATCC 22019). (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.01.031
• 作为产物：
  描述：

  4-苯磺酰苯甲酸 在 硫酸 、 一水合肼 作用下， 以 乙醇 为溶剂， 生成 N1-[4-(phenylsulfonyl)benzoyl]-N4-(4-trifluoromethoxyphenyl)-thiosemicarbazide
  参考文献：
  名称：

  New heterocyclic compounds from 1,2,4-triazole and 1,3,4-thiadiazole class bearing diphenylsulfone moieties. Synthesis, characterization and antimicrobial activity evaluation

  摘要：

  Some new 5-(4-(4-X-phenylsulfonyl)phenyl)-4-(R)-2H-1,2,4-triazol-3(4H)-thiones 4a,b; 5a,b and 5-(4-(4-X-phenylsulfonyl)phenyl)-N-(R)-1,3,4-thiadiazol-2-amines 6a,b; 7a,b were obtained by cyclization of new N-1-[4-(4-X-phenylsulfonyl)benzoyl]-N-4-(R)-thiosemicarbazides 2a,b; 3a,b (X = H, Br). The 1,2,4-triazoles were synthesized by intramolecular cyclization of acylthiosemicarbazides, in basic media. On the other hand, 1,3,4-thiadiazoles were obtained from same acylthiosemicarbazides, in acidic media. These new intermediates from thiosemicarbazide class were afforded by the reaction of 4-(4-X-phenylsulfonyl)benzoic acids hydrazides (X = H, Br) la,b with 4-trifluoromethoxyphenyl or 3,4,5-trimethoxyphenyl isothiocyanate. The newly synthesized compounds were characterized by IR, H-1 NMR, C-13 NMR, MS and elemental analysis. All the new compounds were screened for their antimicrobial activity against some bacteria (Staphylococcus aureus ATCC 25923, Bacillus cereus ATCC 13061, Escherichia coli ATCC 25922, Enterobacter cloacae ATCC 49141, Acinetobacter baumannii ATCC 19606 and Pseudomonas aeruginosa ATCC 27853) and yeasts (Candida albicans ATCC 90028 and Candida parapsilosis ATCC 22019). (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.01.031

文献信息

• New heterocyclic compounds from 1,2,4-triazole and 1,3,4-thiadiazole class bearing diphenylsulfone moieties. Synthesis, characterization and antimicrobial activity evaluation
  作者：Stefania-Felicia Barbuceanu、Gabriel Saramet、Gabriela Laura Almajan、Constantin Draghici、Florica Barbuceanu、Gabriela Bancescu

  DOI：10.1016/j.ejmech.2012.01.031

  日期：2012.3

  Some new 5-(4-(4-X-phenylsulfonyl)phenyl)-4-(R)-2H-1,2,4-triazol-3(4H)-thiones 4a,b; 5a,b and 5-(4-(4-X-phenylsulfonyl)phenyl)-N-(R)-1,3,4-thiadiazol-2-amines 6a,b; 7a,b were obtained by cyclization of new N-1-[4-(4-X-phenylsulfonyl)benzoyl]-N-4-(R)-thiosemicarbazides 2a,b; 3a,b (X = H, Br). The 1,2,4-triazoles were synthesized by intramolecular cyclization of acylthiosemicarbazides, in basic media. On the other hand, 1,3,4-thiadiazoles were obtained from same acylthiosemicarbazides, in acidic media. These new intermediates from thiosemicarbazide class were afforded by the reaction of 4-(4-X-phenylsulfonyl)benzoic acids hydrazides (X = H, Br) la,b with 4-trifluoromethoxyphenyl or 3,4,5-trimethoxyphenyl isothiocyanate. The newly synthesized compounds were characterized by IR, H-1 NMR, C-13 NMR, MS and elemental analysis. All the new compounds were screened for their antimicrobial activity against some bacteria (Staphylococcus aureus ATCC 25923, Bacillus cereus ATCC 13061, Escherichia coli ATCC 25922, Enterobacter cloacae ATCC 49141, Acinetobacter baumannii ATCC 19606 and Pseudomonas aeruginosa ATCC 27853) and yeasts (Candida albicans ATCC 90028 and Candida parapsilosis ATCC 22019). (C) 2012 Elsevier Masson SAS. All rights reserved.