22312-77-2

Basic information

• Product Name: 2-(CHLOROMETHYL)-3-PHENYL-4(3H)-QUINAZOLINONE
• Synonyms: 2-(CHLOROMETHYL)-3-PHENYL-4(3H)-QUINAZOLINONE;2-(chloromethyl)-3-phenyl-3,4-dihydroquinazolin-4-one
• CAS NO: 22312-77-2
• Molecular Formula: C₁₅H₁₁ClN₂O
• Molecular Weight: 270.71
• Mol File: 22312-77-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-(CHLOROMETHYL)-3-PHENYL-4(3H)-QUINAZOLINONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(CHLOROMETHYL)-3-PHENYL-4(3H)-QUINAZOLINONE(22312-77-2)
• EPA Substance Registry System: 2-(CHLOROMETHYL)-3-PHENYL-4(3H)-QUINAZOLINONE(22312-77-2)

Safety Data

• Hazardous Substances Data: 22312-77-2(Hazardous Substances Data)

Upstream product

• 62-53-3 aniline 
• 14422-49-2 2-chloroacetamidobenzoic acid 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 3817-05-8 2-(chloromethyl)quinazolin-4(3H)-one 
• 118-92-3 anthranilic acid 
• 98592-35-9 2-(chloromethyl)-4H-benzo[d][1,3]oxazin-4-one 
• 18871-29-9 2-Chloracetamido-benzoesaeure-anilid 

Downstream Products

• 1189553-14-7 C₂₉H₃₀N₂O₁₀S 
• 1189553-20-5 C₂₆H₂₆N₂O₈S 
• 1250276-65-3 2-(4-methylsulfonylpiperazin-1-ylmethyl)-3-phenylquinazolin-4(3H)-one 
• 1190370-13-8 tert-butyl 4-[(3,4-dihydro-4-oxo-3-phenylquinazolin-2-yl)methyl]piperazine-1-carboxylate 
• 1190370-17-2 3-phenyl-2-(piperazin-1-ylmethyl)quinazolin-4(3H)-one 
• 952612-54-3 N-[5-(4-oxo-3-phenyl-3,4-dihydro-quinazolin-2-yl)-4-phenyl-thiazol-2-yl]-benzamide 

Relevant articles and documents

Substituted 4-phenylthiazoles: Development of potent and selective A1, A3 and dual A1/A3 adenosine receptor antagonists

Adenosine acts as a powerful signaling molecule via four distinct G protein-coupled receptors, designated A1, A2A, A2B and A3 adenosine receptors (ARs). A2A and A2B ARs are Gs-coupled, while A1 and A3 ARs inhibit cAMP production via Gi proteins. Antagonists for A1 and A3 ARs may be useful for the treatment of (neuro)inflammatory diseases including acute kidney injury and kidney failure, pulmonary diseases, and Alzheimer's disease. In the present study, we optimized the versatile 2-amino-4-phenylthiazole scaffold by introducing substituents at N2 and C5 to obtain A1 and A3 AR antagonists including dual-target compounds. Selective A1 antagonists with (sub)nanomolar potency were produced, e.g. 11 and 13. These compounds showed species differences being significantly more potent at the rat as compared to the human A1 AR, and were characterized as inverse agonists. Several potent and selective A3 AR antagonists, e.g. 7, 8, 17 and 22 (Ki values of 5–9 nM at the human A3 AR) were prepared, which were much less potent at the rat orthologue. Moreover, dual A1/A3 antagonists (10, 18) were developed showing Ki values between 8 and 42 nM. Docking and molecule dynamic simulation studies using the crystal structure of the A1 AR and a homology model of the A3 AR were performed to rationalize the observed structure-activity relationships.

Design, synthesis, molecular simulation, and biological activities of novel quinazolinone-pyrimidine hybrid derivatives as dipeptidyl peptidase-4 inhibitors and anticancer agents

Two novel series of quinazolinone-pyrimidine (series a: 9a-9i) and benzyl-pyrimidine hybrids (series b: 12a-12c) were designed, synthesized and characterized by spectroscopic methods. The dipeptidyl peptidase-4 inhibition potencies of these compounds were assessed through a MAK 203 kit. Compound 9e was found to be the most potent agent with an IC50 value of 34.3 ± 3.3 μM. A kinetic study revealed that it acted as a competitive inhibitor. Molecular modeling of these compounds was in agreement with the in vitro results. Due to the crucial role of dipeptidyl peptidase-4 in cancer therapy, the cytotoxic activities of the compounds were also evaluated against three cancerous cell lines (HT-29, SW1116 and A549). Almost all the compounds displayed better antiproliferative activity on colon cancer cell lines (HT-29 and SW1116) compared to a lung cancer cell line (A549). Compounds 9e and 12c exhibited significant activity toward the HT-29 cell line with an IC50 of 10.67 ± 0.3 μM and 27.9 ± 6.5 μM in comparison to sitagliptin and cisplatin as a positive control, respectively. Among the different cells, the compounds showed the best inhibitory effects on HT-29, which was compatible with the greater expression of the dipeptidyl peptidase-4 marker detected by flow cytometry in this cell line. Further studies on the hit compounds (9e and 12c) through cell cycle and apoptosis assays also showed that these compounds could induce cell death by apoptosis or arrest cells in the G2/M phase. Accordingly, the results imply that 9e is a potent inhibitor of dipeptidyl peptidase-4 with efficient anti-cancer activity and could play a role as a cytotoxic agent in colorectal cancer.

Novel 2,4- thiazolidinediones: Synthesis, in?vitro cytotoxic activity, and mechanistic investigation

Two thiazolidinedione scaffolds different in the position of the thiazolidinedione ring in the molecule were tested for in?vitro cytotoxic activity in a panel of human cancer cell lines namely, prostate cancer cells PC-3, breast carcinoma cells MDA-MB-231

Quinazolinone-based rhodanine-3-acetic acids as potent aldose reductase inhibitors: Synthesis, functional evaluation and molecular modeling study

A series of quinazolinone-based rhodanine-3-acetic acids was synthesized and tested for in vitro aldose reductase inhibitory activity. All the target compounds displayed nanomolar activity against the target enzyme. Compounds 3a, 3b, and 3e exhibited almo

Synthesis and screening of 2-(2-(4-substituted piperazine-1-yl)-5- phenylthiazol-4-yl)-3-aryl quinazolinone derivatives as anticancer agents

Synthesis of novel quinazolinone derivatives was performed from the reaction of N-benzoyl substituted piperazine-1-carbothioamide with 2-chloromethyl quinazolinone derivatives and screened for their in vitro cytotoxic activity by MTT assay. The cell lines

Aryne insertion reactions leading to bioactive fused quinazolinones: Diastereoselective total synthesis of cruciferane

Insertion reactions of an in situ generated arynes to a variety of suitably substituted 1,3-quinazolin-4-ones have been demonstrated for a new efficient one-step approach to a diverse range of fused quinazolinone architectures. The present protocol has been effectively utilized to accomplish the concise total synthesis of recently isolated bioactive natural products tryptanthrin, phaitanthrins A-C, and cruciferane.

Synthesis and evaluation of quinazolin-4-ones as hypoxia-inducible factor-1α inhibitors

Quinazolin-4-one 1 was identified as an inhibitor of the HIF-1α transcriptional factor from a high-throughput screen. HIF-1α up-regulation is common in many cancer cells. In this Letter, we describe an efficient one-pot sequential reaction for the synthes

Design, synthesis and evaluation of novel 2-thiophen-5-yl-3H-quinazolin-4-one analogues as inhibitors of transcription factors NF-k{cyrillic}B and AP-1 mediated transcriptional activation: Their possible utilization as anti-inflammatory and anti-cancer ag

In an attempt to discover novel inhibitors of NF-κB and AP-1 mediated transcriptional activation utilizing the concept of chemical lead based medicinal chemistry and bioisosterism a series of 2-(2,3-disubstituted-thiophen-5-yl)-3H-quinazolin-4-one analogs

Synthesis of 2-(4-substitutedsulfonyl piperazin-l-yl-methyl)-3-aryl- quinazolin-4(3H)-one

Reaction of 2-(chloromethyl)-3-arylquinazolin-4(3H)-one 3 with N-BOC piperazine 4 in acetonitrile using K2CO3 and KI, followed by deprotection of BOC group in IPA HC1, gives 3-aryl-2-(piperazin-l-yl) quinazolin-4(3H)-one 6. The latte

Synthesis of novel thioglycoside derivatives containing quinazolinone

Aseries of novel thioglycoside derivatives containing 4(3H)-quinazolinone was designed and synthesized from 2-chloromethyl-quinazolin-4(3H)-ones and 1-thioglycose. Several 2-chloromethyl-quinazolin-4(3H)-ones were synthesized on refluxing with 2-(chloroacetylamino)-benzoic acid and arylamines in acetonitrile. All of the novel compounds were characterized by IR, 1H NMR spectra and elemental analysis. The structures of compounds 7b, 8b and 8c have been determined by X-ray diffraction analysis.