26131-23-7

Basic information

• Product Name: Benzoic acid, 2-hydroxy-, 2-[[(4-chlorophenyl)amino]thioxomethyl]hydrazide
• Synonyms: 1-salicyloyl-4-p-chlorophenyl thiosemicarbazide;1-(2-Hydroxy-benzoyl)-4-(4-chlor-phenyl)-thiosemicarbazid;4-(4-Chlor-phenyl)-1-salicyloyl-thiosemicarbazid;4-(4-chloro-phenyl)-1-salicyloyl thiosemicarbazide;4-(4-Chlorophenyl)-1-salicyl-3-thiosemicarbazide
• CAS NO: 26131-23-7
• Molecular Formula: C14H12ClN3O2S
• Molecular Weight: 321.787
• Mol File: 26131-23-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Benzoic acid, 2-hydroxy-, 2-[[(4-chlorophenyl)amino]thioxomethyl]hydrazide(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoic acid, 2-hydroxy-, 2-[[(4-chlorophenyl)amino]thioxomethyl]hydrazide(26131-23-7)
• EPA Substance Registry System: Benzoic acid, 2-hydroxy-, 2-[[(4-chlorophenyl)amino]thioxomethyl]hydrazide(26131-23-7)

Safety Data

• Hazardous Substances Data: 26131-23-7(Hazardous Substances Data)

Upstream product

• 119-36-8 methyl salicylate 
• 2131-55-7 4-Chlorophenyl isothiocyanate 
• 936-02-7 2-Hydroxybenzoylhydrazine 

Downstream Products

• 172545-17-4 Co⁽²⁺⁾*C₁₄H₁₁N₃O₂SCl^(1-)*CH₃COO^(1-)=Co(C₁₄H₁₁N₃O₂SCl)(CH₃CO₂) 
• 172545-13-0 Ni⁽²⁺⁾*C₁₄H₁₁N₃O₂SCl^(1-)*CH₃COO^(1-)=Ni(C₁₄H₁₁N₃O₂SCl)(CH₃CO₂) 
• 172545-23-2 Cu⁽²⁺⁾*C₁₄H₁₁N₃O₂SCl^(1-)*CH₃COO^(1-)=Cu(C₁₄H₁₁N₃O₂SCl)(CH₃CO₂) 
• 94494-04-9 2-[5-(4-Chloro-phenylamino)-[1,3,4]oxadiazol-2-yl]-phenol 

Relevant articles and documents

1-(2-Hydroxybenzoyl)-thiosemicarbazides are promising antimicrobial agents targeting D-alanine-D-alanine ligase in bacterio

The bacterial cell wall and the enzymes involved in peptidoglycan synthesis are privileged targets for the development of novel antibacterial agents. In this work, a series of 1-(2-hydroxybenzoyl)-thiosemicarbazides inhibitors of D-Ala-D-Ala ligase (Ddl) were designed and synthesized in order to target resistant strains of bacteria. Among these, the 4-(3,4-dichlorophenyl)-1-(2-hydroxybenzoyl)-3-thiosemicarbazide 29 was identified as a potent Ddl inhibitor with activity in the micromolar range. This compound, possessing strong antimicrobial activity including against multidrug resistant strains, was proven to act through a bactericidal mechanism and demonstrated very low cytotoxicity on THP-1 human monocytic cell line. Inhibition of Ddl activity by 29 was confirmed in bacterio using UPLC-MS/MS by demonstrating an increase in D-Ala intracellular pools accompanied by a commensurate decrease in D-Ala-D-Ala. Further structure-activity relationships (SARs) studies provided evidence that the hydroxyl substituent in the 2-position (R1) of the benzoylthiosemicarbazide scaffold is essential for the enzymatic inhibition. This work thus highlights the 1-(2-hydroxybenzoyl)-thiosemicarbazide motif as a very promising tool for the development of novel antibacterial compounds acting through an interesting mechanism of action and low cytotoxicity.

Synthesis and preliminary antibacterial activity of 3-(2-arylamino-1,3,4-thiadiazol-5-yl)-4-hydroxy-4'-substituted sulphamoyl azobenzenes

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