147029-76-3

Usage

Preparation

Preparation by condensation of the Grignard reagent of o-methylanisole with o-toluoyl chloride, followed by demethylation in acid medium of the resultant methyl ether (excellent yield).

Upstream product

• 23597-23-1 2-methyl-benzoic acid o-tolyl ester 
• 95-48-7 ortho-cresol 
• 933-88-0 ortho-toluoyl chloride 
• 14804-31-0 2-methyl-4-bromoanisole 
• 41295-37-8 4-methoxy-2',3-dimethylbenzophenone 

Downstream Products

• 83355-55-9 Acetic acid (2S,3R,4S,5R)-4,5-diacetoxy-2-[2-methyl-4-(2-methyl-benzoyl)-phenoxy]-tetrahydro-pyran-3-yl ester 
• 147029-52-5 Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-[2-methyl-4-(2-methyl-benzoyl)-phenoxy]-tetrahydro-pyran-4-yl ester 
• 1150104-92-9 C₂₂H₂₇NO₂ 
• 83357-08-8 N-{(2S,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-[2-methyl-4-(2-methyl-benzoyl)-phenoxy]-tetrahydro-pyran-3-yl}-acetamide 
• 83355-42-4 [3-Methyl-4-((2S,3R,4S,5R)-3,4,5-trihydroxy-tetrahydro-pyran-2-yloxy)-phenyl]-o-tolyl-methanone 

Relevant academic research and scientific papers

Synthesis, molecular docking, and apoptogenic efficacy of novel N-heterocycle analogs to target B-cell lymphoma 2/X-linked inhibitors of apoptosis proteins to regress melanoma

The novel series of piperidine conjugated benzophenone analogs with amide link 11a–l were synthesized in a multistep process. The structures of these compounds were confirmed by IR, 1H, 13C, NMR, and mass spectra and also by elementa

Design and synthesis of diamide-coupled benzophenones as potential anticancer agents

A series of diamide-coupled benzophenone, 2-(4-benzoyl-phenoxy)-N-{2-[2-(4-benzoyl-phenoxy)-acetylamino]-phenyl}-acetamide analogues (9a-l) were synthesized by multistep reactions and all compounds were well characterized. Among the series (9a-l), compound 9k with three methyl groups at ortho position in rings A, B, and D and bromo group at the para position in ring E was selected as a lead compound by screening through multiple cancer cell types by in-vitro cytotoxic and antiproliferative assay systems. Also, the cytotoxic nature of the compound 9k resulted the regression of the tumor growth in-vivo, which could be due to decreased vascularisation in the peritoneum lining of the mice which regress the tumor growth. The results were reconfirmed in-vivo chorioallantoic membrane model which indicates a scope of developing 9k into potent anticancer drug in near future.

Synthesis and evaluation of novel benzophenone-thiazole derivatives as potent VEGF-A inhibitors

A series of 2-(4-benzoyl-phenoxy)-N-(4-phenyl-thiazol-2-yl)-Acetamides (10a-n) were synthesized by multistep reaction sequence and all the compounds were well characterized for structural elucidation. The in vitro cytotoxicity of compounds 10a-n was evaluated against EAC and DLA cell lines using trypan blue dye exclusion method. Further MTT assay and LDH release assay, followed by in vivo studies on murine model were also evaluated. The compound 10h with a methyl and fluoro groups at benzophenone moiety and methoxy group at phenyl ring was in a leading position to exhibit the promising antiproliferative effect through translational VEGF-A inhibition.

Design, synthesis, and anticancer properties of novel benzophenone- conjugated coumarin analogs

In the current scenario, development of anticancer drugs with specific targets is of prime importance in modern chemical biology. Observing the importance of benzophenone and coumarin nucleus, it would be worthwhile to design and synthesize novel benzophenone derivatives (8a-o) bearing the coumarin nucleus. Further, they were screened for prospective anticancer activities in vitro against the Michigan Cancer Foundation-7 (MCF-7) and Ehrlich's ascites tumor (EAT) cell lines and their biomarkers, followed by in silico studies regarding phosphoinositide 3-kinase (PI3K) and caspase by molecular docking. Benzophenones have been reported as potential drugs targeting tumor angiogenesis; thus, the formation of neovessels in an in vivo model system like CAM, which is angiogenesis dependent, was observed in the presence of compounds 8a-o. The above findings would help in understanding their putative potential as therapeutic agents for cancer patients. Coumarin-integrated benzophenone conjugates (8a-o) were designed, synthesized, and screened for prospective anticancer activities in vitro against the MCF-7 and EAT cell lines. Molecular docking studies with regard to phosphoinositide 3-kinase and caspase were performed. In addition, neovessel formation was observed in an in vivo model system.

Benzophenone-N-ethyl piperidine ether analogues-Synthesis and efficacy as anti-inflammatory agent

A sequence of substituted benzophenone-N-ethyl piperidine ether analogues has been synthesized and evaluated as orally active anti-inflammatory agents with reduced side effects. The anti-inflammatory and ulcerogenic activities of the compounds were compared with naproxen, indomethacin, and phenylbutazone. These analogues showed an interesting anti-inflammatory activity in carrageenan-induced foot pad edema assay. In the air-pouch test, some of the analogues reduced the total number of leukocytes of the exudate, which indicates inhibition of prostaglandin production. Side effects of the compounds were examined on gastric mucosa, in the liver and stomach. None of the compounds illustrated significant side effects compared with standard drugs like indomethacin and naproxen.

Synthesis of benzoyl phenyl benzoates as effective inhibitors for phospholipase A2 and hyaluronidase enzymes

Benzoylation of (hydroxy phenyl) phenyl methanone 2a-g to benzoyl phenyl benzoates 4a-g, a benzophenone analogue, was achieved in good yield. All the newly synthesized compounds were evaluated for their phospholipase A2 [E.C. 3.1.1.4] and hyaluronidase [E.C. 3.2.1.35] enzyme inhibitory activity in snake venom as source and their structure-activity relationship with respect to different groups is reported for the first time. The in vitro PLA2 enzyme inhibitory activity and in vivo anti-inflammatory activity studies of benzoyl phenyl benzoates are illustrated.

Glycosylated Derivatives of Benzophenone, Benzhydrol, and Benzhydril as Potential Venous Antithrombotic Agents

A series of glycosylated derivatives of benzophenone, benzhydrol, and benzhydril has been synthesized and evaluated for potential activity as venous antithrombotic agents.Studies on structure-activity relationships revealed that compounds having an electr