4-p-toluidino-1-(thiophen-2-ylmethylene)thiosemicarbazide | 1435-02-5

• 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: 4-p-toluidino-1-(thiophen-2-ylmethylene)thiosemicarbazide
• 英文别名: thiophen-2-carbaldehyde 4'-(4''-methyl)phenyl-thiosemicarbazone；1-(4-methylphenyl)-3-(thiophen-2-ylmethylideneamino)thiourea
• CAS: 1435-02-5
• 化学式: C₁₃H₁₃N₃S₂
• 分子量: 275.398
• InChiKey: XJKFVVWMXSYEFH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  96.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(2,3-二氯喹喔啉-6-基)磺酰吗啉 、 4-p-toluidino-1-(thiophen-2-ylmethylene)thiosemicarbazide 以 乙腈 为溶剂， 反应 6.0h， 以82%的产率得到6-morpholinosulfonyl-2-((-thiophen-2-ylmethylene)hydrazono)-3-(p-tolyl)-2,3-dihydro-thiazolo[4,5-b]quinoxaline
  参考文献：
  名称：

  Antimicrobial evaluation of thiadiazino and thiazolo quinoxaline hybrids as potential DNA gyrase inhibitors; design, synthesis, characterization and morphological studies

  摘要：

  A series of thiadiazino[5,6-b]quinoxaline and thiazolo[4,5-b]quinoxaline derivatives was designed and synthetized from the reaction of 2,3-dichloro-6-(morpholinosulfonyl)quinoxaline (2) with thiosemicarbazide or thiocarbohydrazide and thiourea derivatives to give nineteen quinoxaline derivatives 3-16. All the synthesized compounds were evaluated for in vitro antimicrobial potential against various bacteria and fungi strains that showed considerable antimicrobial activity against tested microorganisms. The most potent compounds 2, 7, 9, 10, 12 and 13c were exhibited bactericidal activity, in addition to fungistatic activity by dead live assay. Moreover, these compounds showed a significant result against all multi-drug resistance (MDRB) used especially compound 13c that displayed the best results with MICs of MDRB (1.95, 3.9, 2.6, 3.9 mu g/mL) for stains used in this study, compared with Norfloxacin (1.25, 0.78, 1.57, 3.13 mu g/mL). Also, cytotoxicity on normal cell (Vero cells ATCC CCL-81) by MTT assay was performed with lower toxicity results. Additionally, morphological studies, immunostimulatory potency and DNA gyrase inhibition assay of most active compounds was done. A molecular docking study has also been carried out to support the effective binding of the most promising compounds at the active site of the target enzyme S. aureus DNA gyrase (2XCT).

  DOI：

  10.1016/j.bioorg.2020.103841
• 作为产物：
  描述：

  2-噻吩甲醛 、 4-4-甲苯基-3-胺基硫脲 以 乙醇 、 水 为溶剂， 反应 3.0h， 以54%的产率得到4-p-toluidino-1-(thiophen-2-ylmethylene)thiosemicarbazide
  参考文献：
  名称：

  Cyclooctadiene Ru(II) complexes of thiophene-2-carboxaldehyde-derived thiosemicarbazones: synthesis, characterization and antiamoebic activity

  摘要：

  Thiosemicarbazones (TSC) 1-10 were synthesized by condensing substituted thiosemicarbazide with thiophene-2-carboxaldehyde. These thiosemicarbazones were further reacted with [Ru(eta(4)-C8H12)(CH3CN)(2)Cl-2] to forrn complexes of the type [Ru(eta(4) -C8H12)(TSC)Cl-2] 1a-10a. Thiosemicarbazones exhibited antiamoebic activity in the range IC50 = 1.09-5.42 mu M. In vitro assessment of antiamoebic activity indicated that the thiosemicarbazones 3, IC50 = 1.67 mu M, 4, IC50 = 1.11 mu M and 6, IC50 = 1-09 mu M showed substantially less IC50 value than metronidazole (IC50 = 1.87 mu M), a commonly used drug against amoebiasis. Cyclooctadiene Ru(II) complexes of thiosemicarbazones showed significant improvement in antiamoebic activity (IC50 = 0.30-1.39 mu M). All the complexes possess noteworthy potencies and showed less IC50 values than metronidazole against HK-9 strain of Entamoeba histolytica. Among all the complexes, the most promising antiamoebic activities was shown by the complexes 4a and 6a (IC50 = 0.31 mu M of 4a and IC50 = 0.30 mu M of 6a versus metronidazole). (c) 2006 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2006.01.014

文献信息

• Synthesis, Physico-Chemical, and Biological Studies on Oxovanadium(IV) Complexes with Thiosemicarbazones Derived from Thiophene-2-Aldehyde
  作者：S. Yadav、G. K. Pandey、O. P. Pandey、S. K. Sengupta

  DOI：10.1080/00945719708000157

  日期：1997.10

  Oxovanadium(IV) complexes of the types [VOL2] and [VO(LH)(2)]SO4 (where LH = thiosemicarbazones derives from thiophene-2-aldehyde and various substituted thiosemicarbazides) have been synthesized and characterised on the basis of elemental analyses, conductance, magnetic moments and spectral (electronic and IR) data. The antifungal, antiviral and antibacterial activities of the complexes were also investigated.
• Structural and spectroscopic properties of Ru(II) complexes of 4-(aryl)thiosemicarbazones of thiophen-2-carbaldehyde
  作者：Sumita Naskar、Subhendu Naskar、Mike G.B. Drew、Serge I. Gorelsky、Benedikt Lassalle-Kaiser、Ally Aukauloo、Dipankar Mishra、Shyamal Kumar Chattopadhyay

  DOI：10.1016/j.poly.2009.09.030

  日期：2009.12

  Six Ru(II) complexes of formula [Ru(L)(2)(PPh3)(2)] have been prepared where LH = 4-(aryl)thiosemicarbazones of thiophen-2-carbaldehyde. X-ray crystal structures of five of the complexes are reported. In all the complexes ruthenium is six coordinate with a distorted octahedral cis-P-2, cis-N-2, trans-S-2 donor environment, and each of the two thiosemicarbazone ligands are coordinated in a bidentate fashion forming a four membered chelate ring. The complexes undergo a one-electron oxidation at similar to 0.5 V vs. Ag/AgCl. The EPR spectrum of the electrochemically oxidized solution at 100 K shows a rhombic signal, with transitions at g(1) = 2.27, g(2) = 2.00 and g(3) = 1.80. DFT calculations on one of the complexes suggest that there is 35% ruthenium and 17% sulfur orbital contribution to the HOMO. These results suggest that the assignment of metal atom oxidation states in these compounds is not unambiguous. (C) 2009 Elsevier Ltd. All rights reserved.
• Cyclooctadiene Ru(II) complexes of thiophene-2-carboxaldehyde-derived thiosemicarbazones: synthesis, characterization and antiamoebic activity
  作者：Shailendra Singh、Fareeda Athar、Mannar R. Maurya、Amir Azam

  DOI：10.1016/j.ejmech.2006.01.014

  日期：2006.5

  Thiosemicarbazones (TSC) 1-10 were synthesized by condensing substituted thiosemicarbazide with thiophene-2-carboxaldehyde. These thiosemicarbazones were further reacted with [Ru(eta(4)-C8H12)(CH3CN)(2)Cl-2] to forrn complexes of the type [Ru(eta(4) -C8H12)(TSC)Cl-2] 1a-10a. Thiosemicarbazones exhibited antiamoebic activity in the range IC50 = 1.09-5.42 mu M. In vitro assessment of antiamoebic activity indicated that the thiosemicarbazones 3, IC50 = 1.67 mu M, 4, IC50 = 1.11 mu M and 6, IC50 = 1-09 mu M showed substantially less IC50 value than metronidazole (IC50 = 1.87 mu M), a commonly used drug against amoebiasis. Cyclooctadiene Ru(II) complexes of thiosemicarbazones showed significant improvement in antiamoebic activity (IC50 = 0.30-1.39 mu M). All the complexes possess noteworthy potencies and showed less IC50 values than metronidazole against HK-9 strain of Entamoeba histolytica. Among all the complexes, the most promising antiamoebic activities was shown by the complexes 4a and 6a (IC50 = 0.31 mu M of 4a and IC50 = 0.30 mu M of 6a versus metronidazole). (c) 2006 Elsevier SAS. All rights reserved.
• Antimicrobial evaluation of thiadiazino and thiazolo quinoxaline hybrids as potential DNA gyrase inhibitors; design, synthesis, characterization and morphological studies
  作者：Yousry A. Ammar、Awatef A. Farag、Abeer M. Ali、Sadia A. Hessein、Ahmed A. Askar、Eman A. Fayed、Doaa M. Elsisi、Ahmed Ragab

  DOI：10.1016/j.bioorg.2020.103841

  日期：2020.6

  A series of thiadiazino[5,6-b]quinoxaline and thiazolo[4,5-b]quinoxaline derivatives was designed and synthetized from the reaction of 2,3-dichloro-6-(morpholinosulfonyl)quinoxaline (2) with thiosemicarbazide or thiocarbohydrazide and thiourea derivatives to give nineteen quinoxaline derivatives 3-16. All the synthesized compounds were evaluated for in vitro antimicrobial potential against various bacteria and fungi strains that showed considerable antimicrobial activity against tested microorganisms. The most potent compounds 2, 7, 9, 10, 12 and 13c were exhibited bactericidal activity, in addition to fungistatic activity by dead live assay. Moreover, these compounds showed a significant result against all multi-drug resistance (MDRB) used especially compound 13c that displayed the best results with MICs of MDRB (1.95, 3.9, 2.6, 3.9 mu g/mL) for stains used in this study, compared with Norfloxacin (1.25, 0.78, 1.57, 3.13 mu g/mL). Also, cytotoxicity on normal cell (Vero cells ATCC CCL-81) by MTT assay was performed with lower toxicity results. Additionally, morphological studies, immunostimulatory potency and DNA gyrase inhibition assay of most active compounds was done. A molecular docking study has also been carried out to support the effective binding of the most promising compounds at the active site of the target enzyme S. aureus DNA gyrase (2XCT).