78754-81-1

Basic information

• Product Name: 5-chloroquinazoline-2,4-diol
• Synonyms: 5-chloroquinazoline-2,4-diol;5-Chloroquinazoline-2,4(1H,3H)-dione;FR 191863;NSC 338214;5-Chloro-1H-quinazoline-2,4-dione;5-chloro-2,4(1H,3H)-Quinazolinedione
• CAS NO: 78754-81-1
• Molecular Formula: C₈H₅ClN₂O₂
• Molecular Weight: 196.5905
• Mol File: 78754-81-1.mol
• Article Data: 13

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.475g/cm³
• Refractive Index: 1.601
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 9.82±0.20(Predicted)
• CAS DataBase Reference: 5-chloroquinazoline-2,4-diol(CAS DataBase Reference)
• NIST Chemistry Reference: 5-chloroquinazoline-2,4-diol(78754-81-1)
• EPA Substance Registry System: 5-chloroquinazoline-2,4-diol(78754-81-1)

Safety Data

• Hazardous Substances Data: 78754-81-1(Hazardous Substances Data)

Usage

General Description

5-Chloroquinazoline-2,4-diol is a chemical compound belonging to the class of organic compounds known as quinazolines, which are polycyclic aromatic compounds containing a benzene ring fused to a quiazole ring. Its systematic name is 5-Chloro-1H-quinazoline-2,4(3H)-dione. Although there is not much information available regarding this specific chemical, in general, quinazolines and their derivatives can display a wide range of biological activities and are used in pharmaceutical industry. For instance, certain quinazolines have been found to function as anticancer, antiviral, or anti-inflammatory agents, among others. However, the actual properties, uses, and effects of 5-chloroquinazoline-2,4-diol specifically would need to be determined through laboratory study and research.

InChI:InChI=1/C8H5ClN2O2/c9-4-2-1-3-5-6(4)7(12)11-8(13)10-5/h1-3H,(H2,10,11,12,13)

Upstream product

• 54166-95-9 2-amino-6-chlorobenzamide 
• 57-13-6 urea 
• 2148-56-3 2-chloro-6-aminobenzoic acid 
• 6575-11-7 2-amino-6-chlorobenzonitrile 
• 68-12-2 N,N-dimethyl-formamide 
• 590-28-3 potassium cyanate 
• 124-38-9 carbon dioxide 
• 192570-28-8 2-ureido-6-chlorobenzoic acid 

Downstream Products

• 192570-37-9 1-(3,5-di-O-p-toluoyl-2-deoxy-α,β-D-erythro-pentofuranosyl)-5-chloro-quinazoline-2,4(3H)-dione 
• 134517-55-8 2,4,5-trichloroquinazoline 
• 192570-52-8 1-[2-deoxy-5-(4,4'-dimethoxytrityl)-β-D-erythro-pentofuranosyl]-5-chloro-quinazoline-2,4(3H)-dione 
• 192570-57-3 1-[2-deoxy-5-(4,4'-dimethoxytrityl)-α-D-erythro-pentofuranosyl]-5-chloro-quinazoline-2,4(3H)-dione 
• 121496-98-8 6,8-Diethyl-2-phenyl-1,6-dihydro-imidazo[4,5-f]quinazoline-7,9-dione 
• 121496-97-7 6,8-Dimethyl-2-phenyl-1,6-dihydro-imidazo[4,5-f]quinazoline-7,9-dione 

Relevant articles and documents

SUBSTITUTED QUINAZOLINE COMPOUNDS AND PREPARATION AND USES THEREOF

The present invention relates quinazolinone compounds of Formula (I), as well as their preparation and uses, and further relates pharmaceutical compositions comprising these compounds and their uses； wherein the compounds or pharmaceutical compositions disclosed herein can be used for antagonizing the orexin receptor. The present invention also relates to uses of the compounds or pharmaceutical compositions in treating or preventing neurological and psychiatric disorders and diseases of the central nervous system in mammals, especially in humans.

Synthesis and Characterization of Amidato Divalent Lanthanide Complexes and Their Use in Forming 2,4-Quinazolidinones from CO2 and 2-Aminobenzonitriles

Four amidato divalent lanthanide complexes, {LnLn[N(TMS)2]THF}2 [n = 1, Ln = Eu (1); n = 2, Ln = Eu (3), Yb (4); HL1 = tBuC6H4CONHC6H3(iPr)2; HL2 = C6H5CONHC6H3(iPr)2] and {L3Eu[N(TMS)2]THF}{L32Eu(THF)2} (2) [HL3 = ClC6H4CONHC6H3(iPr)2], were synthesized and extensively characterized. This is the first time that the amidato lanthanide amides 1-4 were used to catalyze the reactions of CO2 and 2-aminobenzonitriles to form quinazoline-2,4(1H,3H)-diones at atmospheric pressure. All the complexes efficiently catalyzed the transformation, with complex 3 showing the highest activity. This catalytic system gave good to excellent yields, and good functional group tolerance. Preliminary studies were conducted to investigate the reaction mechanism.

Antileishmanial activity of a series of N2, N 4-disubstituted quinazoline-2,4-diamines

A series of N2,N4-disubstituted quinazoline-2,4- diamines has been synthesized and tested against Leishmania donovani and L. amazonensis intracellular amastigotes. A structure-activity and structure-property relationship study was conducted in part using the Topliss operational scheme to identify new lead compounds. This study led to the identification of quinazolines with EC50 values in the single digit micromolar or high nanomolar range in addition to favorable physicochemical properties. Quinazoline 23 also displayed efficacy in a murine model of visceral leishmaniasis, reducing liver parasitemia by 37% when given by the intraperitoneal route at 15 mg kg-1 day-1 for 5 consecutive days. Their antileishmanial efficacy, ease of synthesis, and favorable physicochemical properties make the N2,N 4-disubstituted quinazoline-2,4-diamine compound series a suitable platform for future development of antileishmanial agents.