884647-32-9

Basic information

• Product Name: 7-chloro-4-isothiocyanatoquinoline
• Synonyms: 7-chloro-4-isothiocyanatoquinoline
• CAS NO: 884647-32-9
• Molecular Formula: C₁₀H₅ClN₂S
• Molecular Weight: 220.6781
• Mol File: 884647-32-9.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 7-chloro-4-isothiocyanatoquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 7-chloro-4-isothiocyanatoquinoline(884647-32-9)
• EPA Substance Registry System: 7-chloro-4-isothiocyanatoquinoline(884647-32-9)

Safety Data

• Hazardous Substances Data: 884647-32-9(Hazardous Substances Data)

Upstream product

• 86-98-6 4,7-dichloroquinoline 
• 1701-93-5 silver thiocyanate 
• 333-20-0 potassium thioacyanate 
• 1147550-11-5 ammonium thiocyanate 

Downstream Products

• 1449376-68-4 C₁₆H₁₃ClN₄O₂S₂ 
• 1449376-69-5 C₂₀H₁₆ClN₅O₃S₂ 
• 1449376-70-8 C₂₁H₁₈ClN₅O₃S₂ 
• 1449376-71-9 C₁₉H₁₄ClN₅O₂S₃ 
• 1449376-72-0 C₂₁H₁₆ClN₅O₂S₂ 
• 1449376-73-1 C₂₀H₁₅ClN₆O₂S₂ 
• 1449376-74-2 C₂₁H₁₇ClN₆O₂S₂ 
• 1423168-20-0 N-(7-chloroquinolin-4-yl)-4-(4-morpholino-6-((4-nitrophenyl)amino)-1,3,5-triazin-2-yl)piperazine-1-carbothioamide 
• 1423168-21-1 N-(7-chloroquinolin-4-yl)-4-(4-hydrazinyl-6-((4-nitrophenyl)amino)-1,3,5-triazin-2-yl)piperazine-1-carbothioamide 
• 1423168-22-2 4-(4-(2-Carbamothioylhydrazinyl)-6-((4-nitrophenyl)amino)-1,3,5-triazin-2-yl)-N-(7-chloroquinolin-4-yl)piperazine-1-carbothioamide 
• 1423168-23-3 N-(7-chloroquinolin-4-yl)-4-(4-((4-nitrophenyl)amino)-6-(o-tolylamino)-1,3,5-triazin-2-yl)piperazine-1-carbothioamide 
• 1423168-24-4 N-(7-chloroquinolin-4-yl)-4-(4-((4-nitrophenyl)amino)-6-(phenylamino)-1,3,5-triazin-2-yl)piperazine-1-carbothioamide 
• 1423168-25-5 2-(4-(4-((7-hloroquinolin-4-yl)carbamothioyl)piperazin-1-yl)-6-((4-nitrophenyl)amino)-1,3,5-triazin-2-yl)hydrazinecarboxamide 
• 1423168-26-6 4-(4-((3-aminopropyl)amino)-6-((4-nitrophenyl)amino)-1,3,5-triazin-2-yl)-N-(7-chloroquinolin-4-yl)piperazine-1-carbothioamide 

Relevant articles and documents

Strong in Vitro Cytotoxic Potential of New Ruthenium-Cymene Complexes

Two p-cymenerutheniumchlorido complexes with thiourea derivative of 7-chloroquinoline (C1) and pyridine-3-imidazole (C2) were synthesized starting from [(η6-p-cymene)RuCl2]2 and corresponding ligands. The structures of complexes were determined with elemental analysis and IR, ESIMS, 1H and 13C{1H} NMR, and 2D 1H-15N correlation NMR spectroscopy. Cytotoxic activities examined by the MTT assay were performed in five human neoplastic cell lines (HeLa, K562, A549, MDA-MB-231, EA.hy926) and one nontumor human fetal lung fibroblast cell line (MRC-5). Tested complexes exhibited low micromolar activities with IC50 in the range 11.03-56.45 μM, while ligands L1 and L2 were significantly less active. Complex C1 showed cytoselective activity toward the K562 cell line (IC50 = 11.03 ± 1.39 μM) and was 3 times less active against the nontumor MRC-5 cell line. Flow cytometry analysis indicated that complexes C1 and C2 after 24 h treatment caused a concentration-dependent increase of the apoptotic sub-G1 fraction (up to 18.4%), comparable to cis-diamminedichloridoplatinum(II) (cisplatin, CDDP), although without other substantial alterations of the cell cycle. A drug-accumulation and DNA-binding study performed by ICP-MS in the K562 cell line revealed that complex C1 had a high intracellular uptake (1.38 μg Ru/106 cells), which significantly exceeded the intracellular uptake levels of CDDP (0.29 μg Pt/106 cells) and C2 (0.08 μg Ru/106 cells). However, both ruthenium complexes C1 and C2 bind to cellular DNA less efficiently in comparison to CDDP. The structure-activity relationship clearly suggested that introduction of a 7-chloroquinoline moiety in the ruthenium(II)-p-cymene complex significantly contributed to the intracellular uptake of C1 and higher cytotoxicity and cytoselectivity. (Graph Presented).

Copper(0) catalyzed C-N coupling approach for the synthesis of thiourea linked quinoline analogues using aqueous media: Rationale and biological study

A convergent and facile synthesis of thiourea-based novel 1-(3-nitrophenyl)-3-(7- (substituted phenylamino/piperazino)quinolin-4-yl)thiourea derivatives is presented by approaching copper catalyzed Ullmann reaction. Pliable route was adopted to achieve amination on bioactive 4,7- dichloroquinoline analogous for the first time in which substituted amine/piperazine condensed with C-7 position of quinoline core. Presented C-N coupling reaction precedes fair to good yields. Cu(0) catalyzed synthetic route was also explained by discussing its probable mechanism. On the basis of currently available antimicrobial drugs, we rationalized the title compounds and examined their biological potency. Compound 3i proved to be the most potent antimicrobial derivative (36 mm, 0.39 μg/mL MIC) against B. cereus strain than standard Ciprofloxacin (31 mm, 0.39 μg/mL MIC). Compound 4e showed equipotent antituberculosis (99% inhibition, 6.25 μg/mL MIC) effect against H37Rv strain as compared to Pyrazinamide. Final analogues were characterized by IR, 1H NMR, 13C NMR, mass spectroscopy and elemental analysis.

Development of 4-aminoquinoline-1,3,5-triazine conjugates as potent antibacterial agent through facile synthetic route

A series of novel hybrid 4-aminoquinoline-1,3,5-triazine derivatives were developed and subsequently tested against representative Gram-positive and Gram-negative microorganisms for determination of their antibacterial activity. Screening results indicate that, title molecule exhibit moderate to potent activity in comparison to standard. These hybrid derivatives were synthesized through a facile synthetic routes and structure of reaction intermediates as well as target molecules were recognised with the aid of various spectroscopic techniques viz., FTIR, NMR, mass and elemental analysis.