59134-89-3

Basic information

• Product Name: 8-CHLORO[1,3]DIOXOLO[4,5-G]QUINOLINE
• Synonyms: 8-CHLORO[1,3]DIOXOLO[4,5-G]QUINOLINE;4-CHLORO-6,7-METHYLENEDIOXYQUINOLINE
• CAS NO: 59134-89-3
• Molecular Formula: C₁₀H₆ClNO₂
• Molecular Weight: 207.61314
• Mol File: 59134-89-3.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 332.739°C at 760 mmHg
• Flash Point: 155.035°C
• Appearance: /
• Density: 1.484g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.686
• CAS DataBase Reference: 8-CHLORO[1,3]DIOXOLO[4,5-G]QUINOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 8-CHLORO[1,3]DIOXOLO[4,5-G]QUINOLINE(59134-89-3)
• EPA Substance Registry System: 8-CHLORO[1,3]DIOXOLO[4,5-G]QUINOLINE(59134-89-3)

Safety Data

• Hazardous Substances Data: 59134-89-3(Hazardous Substances Data)

Usage

General Description

8-Chloro[1,3]dioxolo[4,5-g]quinoline, also known as C-DOQ, is a chemical compound that belongs to the quinoline family. It is a heterocyclic aromatic organic compound containing a quinoline core with two oxygen atoms at positions 1,3 and a chlorine atom at position 8 in the ring structure. C-DOQ is used in the field of medicinal chemistry as a scaffold for designing new compounds with potential biological activities. It has been studied for its potential as an antimicrobial and antimalarial agent due to its ability to inhibit the growth of certain microorganisms and parasites. Additionally, C-DOQ has shown promise in the development of new drugs for the treatment of various diseases.

InChI:InChI=1/C10H6ClNO2/c11-7-1-2-12-8-4-10-9(3-6(7)8)13-5-14-10/h1-4H,5H2

Upstream product

• 35478-79-6 4-hydroxy-6,7-methylenedioxyquinoline 
• 17394-77-3 diethyl [[3,4-(methylenedioxy)phenylamino]methylene]malonate 
• 14205-65-3 ethyl 8-hydroxy-1,3-dioxolo[4,5-g]quinoline-7-carboxylate 
• 74-97-5 chlorobromomethane 
• 593-71-5 Chloroiodomethane 
• 35654-56-9 6,7-dimethoxy-4-chloroquinoline 
• 26893-27-6 8-hydroxy-1,3-dioxolo[4,5-g]quinoline-7-carboxylic acid 
• 14268-66-7 benzo[1,3]dioxolo-5-ylamine 
• 28657-75-2 2-amino-4,5-methylenedioxy-acetophenone 
• 154504-43-5 6,7-methylenedioxy-4-quinolone 

Downstream Products

• 86749-73-7 6,7-methylenedioxy-4-phenoxyquinoline 
• 847573-72-2 4-[[2-(N-benzyl-N-tert-butylamino)ethyl]amino]-6,7-methylenedioxyquinoline 
• 847573-71-1 4-[[2-(N-benzyl-N-isopropylamino)ethyl]amino]-6,7-methylenedioxyquinoline 
• 847573-77-7 4-[[2-(4-benzylpiperazin-1-yl)ethyl]amino]-6,7-methylenedioxyquinoline 
• 1489230-70-7 C₃₃H₄₀BrN₅O₉ 
• 1489230-67-2 C₃₂H₃₈BrN₅O₉ 
• 1489230-64-9 C₃₁H₃₆BrN₅O₉ 
• 1489230-74-1 C₃₅H₄₄BrN₅O₉ 
• 1489230-73-0 C₃₄H₄₂BrN₅O₉ 
• 529488-54-8 N-(6,7-methylenedioxyquinolin-4-yl)-N-[2-(2-(t-butyldimethylsilanyloxy)ethoxy)ethyl]-2-iodo-4,5-dimethoxybenzamide 
• 529488-55-9 N-(6,7-methylenedioxyquinolin-4-yl)-N-[1-[(t-butyldimethylsilanyloxy)methyl]-N-2-dimethylaminoethyl]-2-iodo-4,5-dimethoxybenzamide 
• 529488-47-9 N-(6,7-methylenedioxyquinolin-4-yl)-N-[2-(4-methyl-1-piperazinyl)ethyl]-2-iodo-4,5-dimethoxybenzamide 
• 529488-53-7 N-(6,7-methylenedioxyquinolin-4-yl)-N-[2-(t-butyldimethylsilanyloxy)ethyl]-2-iodo-4,5-dimethoxybenzamide 
• 529488-46-8 N-(6,7-methylenedioxyquinolin-4-yl)-N-[(2-pyrrolidin-1-yl)ethyl]-2-iodo-4,5-dimethoxybenzamide 

Relevant articles and documents

INDOLEAMINE 2,3-DIOXYGENASE INHIBITORS AND USE OF SAME IN MEDICINE

The present invention relates to a compound represented by formula I, a pharmaceutical composition containing the compound of formula I, a method for inhibiting indoleamine 2,3-dioxygenase, and its use in medicine.

METHODS FOR TREATING HEMATOLOGICAL MALIGNANCIES

The invention provides methods and pharmaceutical compositions for treating certain hematological cancers

5-(2-Aminoethyl)dibenzo[c,h][1,6]naphthyridin-6-ones: Variation of N-alkyl substituents modulates sensitivity to efflux transporters associated with multidrug resistance

5H-8,9-Dimethoxy-5-(2-N,N-dimethylaminoethyl)-2,3-methylenedioxydibenzo[c, h]-[1,6]naphthyridin-6-one (ARC-111) has potent TOP1-targeting activity and pronounced antitumor activity. Several analogues of ARC-111 were synthesized with NH2, N-alkyl, N,N-dialkyl, pyrrolidinyl, piperidinyl, and piperazinyl substituents at the 2-position of the 5-ethyl group. The relative TOP1-targeting activity and cytotoxicity of these structural analogues were assessed in RPMI8402 and P388 tumor cells and their camptothecin-resistant variants CPT-K5 and P388/CPT45, respectively. Potent TOP1-targeting activity was retained within a series of mono N-alkyl analogues that included NHCH 2CH3, NHCH(CH3)2, and NHC(CH 3)3. TOP1-targeting activity was diminished by the presence of a N-benzyl moiety. In a comparison of a series of N-alkyl-N-isopropyl analogues, activity decreased in the order CH3 > CH2CH3 > CH-(CH3)2. Cytotoxicity in RPMI8402 and P388 did correlate with TOP1-targeting activity. Cytotoxic activity was also determined in KB3-1 cells and its variants KB/V-1 and KBH5.0. As KB/V-1 cells overexpress MDR1 and KBH5.0 cells overexpress BCRP, decreased cytotoxicity in these cell lines relative to the parent cell line is indicative of compounds that are substrates for these efflux transporters. In view of their diminished cytotoxicity in KB/V-1 cells, it appears that the likely demethylated metabolites of ARC-111, i.e., where NH2 or NHCH3 replaces the N(CH3)2 at the 2-position of the 5-ethyl substituent, are substrates for MDR1. In contrast, no significant difference in cytotoxicity among these three cell lines was observed with other N-alkyl analogues, including NHC2H5, NHCH(CH 3)2, NHC(CH3)3, N(CH 3)2, N(CH2CH3)2, NCH 3(CH-(CH3)2), and either the pyrrolidinyl or the piperidinyl analogues. The 2-(piperazinyl) analogues were associated with diminished cytotoxicity in KB/V-1 cells, suggesting that the second basic amino substituent is associated with their recognition as substrates by MDR1. Comparative studies on the antitumor activity of ARC-111 and its N-demethylated derivatives (the NHCH3 and NH2 analogues) against SJ-BT45 medulloblastoma xenografts in seid mice revealed that the secondary amine metabolite is at least as active as ARC-111 in vivo, although the primary amine derivative was significantly less potent.