59870-43-8

Basic information

• Product Name: 2-CHLOROQUINAZOLIN-4-AMINE
• Synonyms: IFLAB-BB F2108-0111;2-CHLOROQUINAZOLIN-4-AMINE;Nsc75185;2-Chloroquinazolin-4-ylamine;2-chloro-4-Quinazolinamine;2-Chloro-4-aminoquinazoline;4-Quinazolinamine,2-chloro-;4-Amino-2-chloroquinazoline
• CAS NO: 59870-43-8
• Molecular Formula: C₈H₆ClN₃
• Molecular Weight: 179.61
• Mol File: 59870-43-8.mol

Chemical Properties

• Boiling Point: 313.6 °C at 760 mmHg
• Flash Point: 143.5 °C
• Appearance: /
• Density: 1.445g/cm³
• Vapor Pressure: 0.00049mmHg at 25°C
• Refractive Index: 1.726
• Storage Temp.: 2-8°C(protect from light)
• CAS DataBase Reference: 2-CHLOROQUINAZOLIN-4-AMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CHLOROQUINAZOLIN-4-AMINE(59870-43-8)
• EPA Substance Registry System: 2-CHLOROQUINAZOLIN-4-AMINE(59870-43-8)

Safety Data

• Hazardous Substances Data: 59870-43-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Chloroquinazolin-4-amine is used as a key intermediate for the synthesis of various pharmaceuticals, leveraging its potential biological and pharmacological activities. Its derivatives are particularly studied for their antitumor capabilities, offering a promising avenue for the development of novel cancer treatments.
Used in Organic Synthesis:
In the field of organic synthesis, 2-chloroquinazolin-4-amine serves as a valuable building block, enabling the creation of a diverse array of organic compounds. Its unique structure and functional groups facilitate its incorporation into complex molecular frameworks, contributing to the advancement of organic chemistry.
Used in Drug Discovery:
2-Chloroquinazolin-4-amine is utilized in drug discovery processes, where its derivatives are explored for their potential as enzyme inhibitors. This application is crucial for identifying new therapeutic agents that can modulate enzyme activity, thereby addressing various disease conditions.
Used in Enzyme Inhibition Research:
2-Chloroquinazolin-4-amine and its derivatives are employed in research aimed at understanding and inhibiting the activity of specific enzymes. This research is vital for developing targeted therapies that can effectively manage enzyme-related diseases and disorders.

InChI:InChI=1/C8H6ClN3/c9-8-11-6-4-2-1-3-5(6)7(10)12-8/h1-4H,(H2,10,11,12)

Upstream product

• 607-68-1 2,4-dichloroquinazoline 
• 118-92-3 anthranilic acid 
• 86-96-4 quinazoline-2,4-diol 
• 1336-21-6 ammonium hydroxide 
• 86-96-4 1,2,3,4-tetrahydro-quinazoline-2,4-dione 
• 67-56-1 methanol 
• 77767-98-7 2-chloro-4-methoxyquinazoline 
• 7664-41-7 ammonia 

Downstream Products

• 455266-09-8 N₂-[1-(2-Phenyl-ethanesulfonyl)-piperidin-4-ylmethyl]-quinazoline-2,4-diamine 
• 139308-45-5 N²-phenylquinazoline-2,4-diamine 
• 1022-44-2 4-amino-2-phenyl-quinazoline 
• 749866-16-8 4-amino-2-[trans-(4-aminomethylcyclohexyl)methyamino]quinazoline 
• 253192-03-9 4-[1-(4-Aminoquinazolin-2-yl)piperidin-4-ylamino]benzoic acid tert-butyl ester 

Relevant articles and documents

BETA-ADRENERGIC RECEPTOR ALLOSTERIC MODULATORS

Provided herein are modulators of beta-adrenergic receptors.

Sulfur and selenium derivatives of quinazoline and pyrido[2,3-d]pyrimidine: Synthesis and study of their potential cytotoxic activity in vitro

The synthesis, cytotoxic activities and selectivities of 35 derivatives related to quinazoline and pyrido[2,3-d]pyrimidine are described. The synthesized compounds were screened in vitro against four tumoral cell lines - leukemia (CCRF-CEM), colon (HT-29), lung (HTB-54) and breast (MCF-7) - and two cell lines derived from non-malignant cell lines, one mammary (184B5) and one from bronchial epithelium (BEAS-2B). MCF-7 and HTB-54 were the most sensitive cell lines with GI50 values below 10 μM for eleven and ten compounds, respectively. Two compounds (2o and 3a) were identified that evoked a marked cytotoxic effect in all cell lines tested and one compound, 7h, was potent and selective against MCF-7. A preliminary study into the mechanism of the potent derivatives 2o, 3a and 7h indicated that the cytotoxic activities of these compounds might be mediated by inducing cell death without affecting cell cycle phases.

Design, synthesis, and structure-activity relationships of highly potent 5-HT3 receptor ligands

The 5-HT3 receptor, a pentameric ligand-gated ion channel (pLGIC), is an important therapeutic target. During a recent fragment screen, 6-chloro-N-methyl-2-(4-methyl-1,4-diazepan-1-yl)quinazolin-4-amine (1) was identified as a 5-HT3R hit fragment. Here we describe the synthesis and structure-activity relationships (SAR) of a series of (iso)quinoline and quinazoline compounds that were synthesized and screened for 5-HT3R affinity using a [3H]granisetron displacement assay. These studies resulted in the discovery of several high affinity ligands of which compound 22 showed the highest affinity (pKi > 10) for the 5-HT3 receptor. The observed SAR is in agreement with established pharmacophore models for 5-HT3 ligands and is used for ligand-receptor binding mode prediction using homology modeling and in silico docking approaches.

USE OF COMPOUNDS FOR PREPARING ANTI-TUBERCULOSIS AGENTS

Compounds of a compound of compound of general formula (I) wherein X1, X2, A, R1R2, R3 and R4 are as defined herein; are useful as anti-mycobacterial agents, especially agents for the treatment of tuberculosis.

MODULATION OF CHEMOSENSORY RECEPTORS AND LIGANDS ASSOCIATED THEREWITH

The present invention provides screening methods for identifying modifiers of chemosensory receptors and their ligands, e.g., by determining whether a test entity is suitable to interact with one or more interacting sites within the Venus flytrap domains of the chemosensory receptors as well as modifiers capable of modulating chemosensory receptors and their ligands.

Discovery of quinazolines as histamine H4 receptor inverse agonists using a scaffold hopping approach

From a series of small fragments that was designed to probe the histamine H4 receptor (H4R), we previously described quinoxaline-containing fragments that were grown into high affinity H 4R ligands in a process that was guided by pharmacophore modeling. With a scaffold hopping exercise and using the same in silico models, we now report the identification and optimization of a series of quinazoline-containing H4R compounds. This approach led to the discovery of 6-chloro-N-(furan-3-ylmethyl)2-(4-methylpiperazin-1-yl)quinazolin-4-amine (VUF10499, 54) and 6-chloro-2-(4-methylpiperazin-1-yl)-N-(thiophen-2-ylmethyl) quinazolin-4-amine (VUF10497, 55) as potent human H4R inverse agonists (pKi ) 8.12 and 7.57, respectively). Interestingly, both compounds also possess considerable affinity for the human histamine H 1 receptor (H1R) and therefore represent a novel class of dual action H1R/H4R ligands, a profile that potentially leads to added therapeutic benefit. Compounds from this novel series of quinazolines are antagonists at the rat H4R and were found to possess anti-inflammatory properties in vivo in the rat.

Discovery of 4-(dimethylamino)quinazolines as potent and selective antagonists for the melanin-concentrating hormone receptor 1

A series of 4-(dimethylamino)quinazoline based antagonists of the melanin-concentrating hormone receptor 1 (MCH-R1) is described. This series was derived from a lead compound, AR129330, identified by HTS of a GPCR-directed library using a functional assay with a constitutively activated (CART) form of the receptor. The preliminary optimization resulted in the identification of compounds 20, 21, and 23.

Integrin antagonists

This invention relates to novel heterocycles which are useful as antagonists of the αvβ3 integrin, the α2bβ3 integrin, and related cell surface adhesive protein receptors, to pharmaceutical compositions containing such compounds, processes for preparing such compounds, and to methods of using these compounds, alone or in combination with other therapeutic agents, for the inhibition of cell adhesion, the treatment of angiogenic disorders, inflammation, bone degradation, cancer metastasis, diabetic retinopathy, thrombosis, restenosis, macular degeneration, and other conditions mediated by cell adhesion and/or cell migration and/or angiogenesis.

Design, synthesis and SAR of a series of 2-substituted 4-amino-quinazoline neuropeptide Y Y5 receptor antagonists

The design of a novel series of NPY-Y5 receptor antagonists is described. Key elements for the design were the identification of weak Y5 hits from a Y1 program, results from a combinatorial approach and database mining. This led to the discovery of the quinazoline 4 and the aryl-sulphonamide moiety as major components of the pharmacophore for Y5 affinity. The synthesis and SAR towards CGP71683A is described. (C) 2000 Elsevier Science Ltd. All rights reserved.

Process for preparing quinazolines

2-Halo-4-aminoquinazolines are produced by a two-step process involving cyclization of 1-phenyl-3-cyanoureas or 1-phenyl-3-cyanothioureas in the presence of phosphorus halides and phosphorus oxyhalides to provide a phosphoquinazoline intermediate which is hydrolyzed to the quinazoline. Exemplary of the process is the intramolecular cyclization of 1-(3,4-dimethoxyphenyl)-3-cyanourea in the presence of phosphorus pentachloride and phosphorus oxychloride to a phosphoquinazoline intermediate which is subsequently hydrolyzed with formic acid to 2-chloro-4-amino-6,7-dimethoxy-quinazoline. The 2-halo-4-aminoquinazolines of the instant process are particularly valuable as intermediates in the preparation of 4-amino-2-(4-substituted-piperazin-l-yl)quinazolines useful in the treatment of cardiovascular disease, e.g. hypertension.