5315-86-6

Basic information

• Product Name: 2-(4-chlorobenzylidene)hydrazinecarboxamide
• CAS NO: 5315-86-6
• Molecular Formula: C₈H₈ClN₃O
• Molecular Weight: 197.6216
• Mol File: 5315-86-6.mol
• Article Data: 25

Chemical Properties

• Density: 1.35g/cm³
• Refractive Index: 1.607
• CAS DataBase Reference: 2-(4-chlorobenzylidene)hydrazinecarboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-chlorobenzylidene)hydrazinecarboxamide(5315-86-6)
• EPA Substance Registry System: 2-(4-chlorobenzylidene)hydrazinecarboxamide(5315-86-6)

Safety Data

• Hazardous Substances Data: 5315-86-6(Hazardous Substances Data)

Usage

Compound type

Hydrazine derivative

Contains

Benzylidene group and carboxamide group

Common uses

Pharmaceutical industry for potential antitumor and antiviral properties

Studied for

Inhibiting cancer cell growth and treating viral infections

Potential applications

Immunosuppressant and treatment for autoimmune diseases

Research interest

Medicine and pharmacology fields

Upstream product

• 104-88-1 4-chlorobenzaldehyde 
• 4426-72-6 hydrazine carboxamide 
• 75586-46-8 2-(4-chlorophenyl)-4-oxo-2,3-dihydrobenzopyrano<2,3-d>pyrimidine 
• 79-19-6 thiosemicarbazide 
• 104-83-6 1-Chloro-4-(chloromethyl)benzene 
• 106-43-4 para-chlorotoluene 
• 563-41-7 semicarbazide hydrochloride 
• 106737-90-0 C₈H₁₀ClN₃O₂ 

Downstream Products

• 103853-47-0 [2-(4-chloro-phenyl)-4-oxo-thiazolidin-3-yl]-urea 
• 62329-42-4 {[5-(4-chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-thiocarbamoylsulfanyl}-acetic acid 
• 180045-63-0 C₁₂H₁₇ClN₄O₂ 
• 176248-88-7 [5-(4-Chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-(2,2,2-trichloro-1-phenyl-ethyl)-amine 
• 177589-02-5 [5-(4-Chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-[2,2,2-trichloro-1-(4-chloro-phenyl)-ethyl]-amine 
• 176248-87-6 [5-(4-Chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-[2,2,2-trichloro-1-(4-fluoro-phenyl)-ethyl]-amine 
• 333719-64-5 (Ru((C₆H₅)3P)2(ClC₆H₄CHNNCONH₂)(CO)Cl) 
• 333719-64-5 (Ru((C₆H₅)3P)2(ClC₆H₄CHNNCONH₂)(CO)Cl) 
• 33199-40-5 C₈H₆ClN₃O 
• 1261138-30-0 C₂₂H₁₃ClN₄O₂ 
• 385821-38-5 methyl (2-(2-(4-chlorobenzyldene)hydrazono)-4-oxothiazolidin-5-ylidene)acetate 
• 33621-61-3 2-amino-5-(4-chlorophenyl)-1,3,4-oxadiazole 
• 1258277-20-1 2-[2-(4-chlorophenyl)-1,3,4-thiadiazol-5-yl] benzisoselenazol-3(2H)-one 

Relevant articles and documents

Ultrapotent Inhibitor of Clostridioides difficile Growth, Which Suppresses Recurrence in Vivo

Clostridioides difficile is the leading cause of healthcare-associated infection in the U.S. and considered an urgent threat by the Centers for Disease Control and Prevention (CDC). Only two antibiotics, vancomycin and fidaxomicin, are FDA-approved for the treatment of C. difficile infection (CDI), but these therapies still suffer from high treatment failure and recurrence. Therefore, new chemical entities to treat CDI are needed. Trifluoromethylthio-containing N-(1,3,4-oxadiazol-2-yl)benzamides displayed very potent activities [sub-μg/mL minimum inhibitory concentration (MIC) values] against Gram-positive bacteria. Here, we report remarkable antibacterial activity enhancement via halogen substitutions, which afforded new anti-C. difficile agents with ultrapotent activities [MICs as low as 0.003 μg/mL (0.007 μM)] that surpassed the activity of vancomycin against C. difficile clinical isolates. The most promising compound in the series, HSGN-218, is nontoxic to mammalian colon cells and is gut-restrictive. In addition, HSGN-218 protected mice from CDI recurrence. Not only does this work provide a potential clinical lead for the development of C. difficile therapeutics but also highlights dramatic drug potency enhancement via halogen substitution.

Biological evaluation of arylsemicarbazone derivatives as potential anticancer agents

Fourteen arylsemicarbazone derivatives were synthesized and evaluated in order to find agents with potential anticancer activity. Cytotoxic screening was performed against K562, HL-60, MOLT-4, HEp-2, NCI-H292, HT-29 and MCF-7 tumor cell lines. Compounds 3c and 4a were active against the tested cancer cell lines, being more cytotoxic for the HL-60 cell line with IC50 values of 13.08 μμM and 11.38 μμM, respectively. Regarding the protein kinase inhibition assay, 3c inhibited seven different kinases and 4a strongly inhibited the CK1δ/ε kinase. The studied kinases are involved in several cellular functions such as proliferation, migration, cell death and cell cycle progression. Additional analysis by flow cytometry revealed that 3c and 4a caused depolarization of the mitochondrial membrane, suggesting apoptosis mediated by the intrinsic pathway. Compound 3c induced arrest in G1 phase of the cell cycle on HL-60 cells, and in the annexin V assay approximately 50% of cells were in apoptosis at the highest concentration tested (26 μμM). Compound 4a inhibited cell cycle by accumulation of abnormal postmitotic cells at G1 phase and induced DNA fragmentation at the highest concentration (22 μμM).

Synthesis and antimicrobial evaluation of novel 3-(arylideneamino)-3a,8a-dihydroxy-1,3,3a,8a-tetrahydroindeno[1,2-d]imidazole-2,8-diones and their 2-thioxo analogues

The preparation of some novel 3-(arylideneamino)-3a,8a-dihydroxy-1,3,3a,8a-tetrahydroindeno[1,2-d]imidazole-2,8-diones 8(i–xiv) and 3-(arylideneamino)-3a,8a-dihydroxy-2-thioxo-1,3,3a,8a-tetrahydroindeno[1,2-d]imidazol-8(2H)-ones 9(i–xiv) have been reported through one-pot catalyst-free reaction of aldehydes, semicarbazide hydrochloride/thiosemicarbazide with ninhydrin. All the synthesized compounds have been screened for antimicrobial activity and some of them were observed to possess broad spectrum antibacterial potential as well as significant antagonistic potential against fungal pathogens.