923289-39-8

Basic information

• Product Name: 4-Quinolinol, 8-chloro-7-methoxy-2-[4-(1-methylethyl)-2-thiazolyl]-
• Synonyms: 4-Quinolinol, 8-chloro-7-methoxy-2-[4-(1-methylethyl)-2-thiazolyl]-;8-chloro-2-(4-isopropylthiazol-2-yl)-7-methoxyquinolin-4-ol;8-Chloro-7-methoxy-2-[4-(1-methylethyl)-2-thiazolyl]-4-quinolinol;8-chloro-7-Methoxy-2-[4-(1-Methylethyl)-2-thiazolyl]-
• CAS NO: 923289-39-8
• Molecular Formula: C16H15ClN2O2S
• Molecular Weight: 334.82
• Product Categories: API intermediates;Heterocycles
• Mol File: 923289-39-8.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 536.2 ºC at 760 mmHg
• Flash Point: 278.1 ºC
• Appearance: /
• Density: 1.343
• Vapor Pressure: 4.1E-12mmHg at 25°C
• Refractive Index: 1.649
• PKA: 6.23±0.40(Predicted)
• CAS DataBase Reference: 4-Quinolinol, 8-chloro-7-methoxy-2-[4-(1-methylethyl)-2-thiazolyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Quinolinol, 8-chloro-7-methoxy-2-[4-(1-methylethyl)-2-thiazolyl]-(923289-39-8)
• EPA Substance Registry System: 4-Quinolinol, 8-chloro-7-methoxy-2-[4-(1-methylethyl)-2-thiazolyl]-(923289-39-8)

Safety Data

• Hazardous Substances Data: 923289-39-8(Hazardous Substances Data)

Usage

General Description

4-Quinolinol, 8-chloro-7-methoxy-2-[4-(1-methylethyl)-2-thiazolyl]- is a chemical compound with a molecular structure that includes a quinolinol ring with a chlorine atom at position 8, a methoxy group at position 7, and a 2-[4-(1-methylethyl)-2-thiazolyl] substituent. 4-Quinolinol, 8-chloro-7-methoxy-2-[4-(1-methylethyl)-2-thiazolyl]- is commonly referred to as clofoctol and is used as an antibacterial agent. Clofoctol has been shown to have activity against a range of gram-positive and gram-negative bacteria, making it a promising candidate for the treatment of various infections. Additionally, clofoctol has also been studied for its potential use in combination therapies for enhancing the efficacy of antibiotics against multidrug-resistant bacteria.

InChI:InChI=1/C16H15ClN2O2S/c1-8(2)11-7-22-16(19-11)10-6-12(20)9-4-5-13(21-3)14(17)15(9)18-10/h4-8H,1-3H3,(H,18,20)

Upstream product

• 923289-37-6 N-(6-acetyl-2-chloro-3-methoxyphenyl)-4-isopropylthiazole-2-carboxamide 

Relevant articles and documents

MACROCYCLIC SERINE PROTEASE INHIBITORS

Provided herein are macrocyclic serine protease inhibitor compounds, for example, of Formula I, pharmaceutical compositions comprising such compounds, and processes of preparation thereof. Also provided are methods of their use for the treatment of an HCV infection in a host in need thereof.

Discovery of novel potent and selective dipeptide hepatitis C virus NS3/4A serine protease inhibitors

Starting from the previously reported HCV NS3/4A protease inhibitor BILN 2061 (1), we have used a fast-follower approach to identify a novel series of HCV NS3/4A protease inhibitors in which (i) the P3 amino moiety and its capping group have been truncated, (ii) a sulfonamide is introduced in the P1 cyclopropyl amino acid, (iii) the position 8 of the quinoline is substituted with a methyl or halo group, and (iv) the ring size of the macrocycle has been reduced to 14 atoms. SAR analysis performed with a limited set of compounds led to the identification of N-{17-[8-chloro-2-(4-isopropylthiazol-2-yl)-7-methoxyquinolin-4-yloxy]-2,14-dioxo-3,15-diazatricyclo [13.3.0.0 [Bartenschlager, R.; Lohmann, V. J. Gen. Virol. 2000, 81, 1631; Vincent Soriano, Antonio Madejon, Eugenia Vispo, Pablo Labarga, Javier Garcia-Samaniego, Luz Martin-Carbonero, Julie Sheldon, Marcelle Bottecchia, Paula Tuma, Pablo Barreiro Expert Opin. Emerg. Drugs, 2008, 13, 1-19]]octadec-7-ene-4-carbonyl}(1-methylcyclopropyl)(1-methylcyclopropyl)sulfonamide 19l an extremely potent (Ki = 0.20 nM, EC50 = 3.7 nM), selective, and orally bioavailable dipeptide NS3/4A protease inhibitor, which has features attractive for further preclinical development.

MACROCYLIC INHIBITORS OF HEPATITIS C VIRUS

Inhibitors of HCV of formula (I), and the N-oxides, salts, and stereochemically isomeric forms thereof, wherein R1 is aryl or a saturated, a partially unsaturated or completely unsaturated 5 or 6 membered monocyclic or 8 to 12 membered bicyclic heterocyclic ring system containing one nitrogen, and optionally one to three oxygen, sulfur or nitrogen, wherein said ring system may be optionally substituted; L is a direct bond, -O-. -O-C1-4alkanediyl-, -O-CO-, -O-C(=O)-NR5a- or -O-C(=O)-NR5a-C1-4alkanediyl-; R2 is hydrogen, -OR6, -C(O)OR6, -C(=O)R7, -C(=O)NR5aR5b, -C(=O)NHR5c, -NR5aR5b, -NHR5c, -NHSOpNR5aR5b, -NR5aSOpR8, or -B(OR6)2; R3 and R4 are hydrogen or C1-6alkyl; or R3 and R4 taken together may form a C3-7cycloalkyl ring; n is 3, 4, 5, or 6; p is 1 or 2; aryl is phenyl, naphthyl, indanyl, or 1,2,3,4-tetrahydronaphthyl, each of which may be optionally substituted Het is a 5 or 6 membered saturated, partially unsaturated or completely unsaturated heterocyclic ring containing 1 to 4 heteroatoms each independently selected from nitrogen, oxygen and sulfur, being optionally condensed with a benzene ring, and wherein the group Het as a whole may be optionally substituted ; pharmaceutical compositions containing compounds (I) and processes for preparing compounds (I). Bioavailable combinations of the inhibitors of HCV of formula (I) with ritonavir are also provided.