5336-56-1Relevant academic research and scientific papers
Synthesis, characterization, docking study and antimicrobial activity of 2-(4-benzoylphenoxy)-1-[2-(1-methyl-1H-indol-3-yl)methyl)-1H-benzo[d]imidazol-1-yl] ethanone derivatives
Prashanth,Ranganatha, V. Lakshmi,Ramu, Ramith,Mandal, Subhankar P.,Mallikarjunaswamy,Khanum, Shaukath Ara
, p. 2741 - 2756 (2021/03/29)
The occurrence of drug-resistant bacterial infections impulses the development of new antibacterial agents that own a mechanism of action different from traditional antibiotics. From the earlier days, benzophenone, indole and benzimidazole moieties alone
Isothiourea-catalyzed enantioselective α-alkylation of esters via 1,6-conjugate addition to para-quinone methides
Arokianathar, Jude N.,Greenhalgh, Mark D.,Hartley, Will C.,McLaughlin, Calum,Ng, Sean,Slawin, Alexandra M. Z.,Smith, Andrew D.,Stead, Darren
supporting information, (2021/11/01)
The isothiourea-catalyzed enantioselective 1,6-conjugate addition of para-nitrophenyl esters to 2,6-disubstituted para-quinone methides is reported. para-Nitrophenoxide, generated in situ from initial N-acylation of the isothiourea by the para-nitrophenyl ester, is proposed to facilitate catalyst turnover in this transformation. A range of para-nitrophenyl ester products can be isolated, or derivatized in situ by addition of benzylamine to give amides at up to 99% yield. Although low diastereocontrol is observed, the diastereoisomeric ester products are separable and formed with high enantiocontrol (up to 94:6 er).
TBAB-catalyzed 1,6-conjugate sulfonylation of paraquinone methides: A highly efficient approach to unsymmetrical gem-diarylmethyl sulfones in water ?
Liu, Zhang-Qin,You, Peng-Sheng,Zhang, Liang-Dong,Liu, Da-Qing,Liu, Sheng-Shu,Guan, Xiao-Yu
supporting information, (2020/02/11)
A highly efficient sulfonylation of para-quinone methides with sulfonyl hydrazines in water has been developed on the basis of the mode involving a tetrabutyl ammonium bromide (TBAB)-promoted sulfa-1,6-conjugated addition pathway. This reaction provides a green and sustainable method to synthesize various unsymmetrical diarylmethyl sulfones, showing good functional group tolerance, scalability, and regioselectivity. Further transformation of the resulting diarylmethyl sulfones provides an efficient route to some functionalized molecules.
Site-selective Oxidative Dearomatization of Phenols and Naphthols into ortho-Quinols or Epoxy ortho-Quinols using Oxone as the Source of Dimethyldioxirane
Cabrera-Afonso, María J.,Carre?o, M. Carmen,Urbano, Antonio
supporting information, (2019/08/21)
A novel reactivity of dimethyldioxirane, generated in situ from Oxone and acetone, with substituted phenols and naphthols is reported. This methodology allowed the synthesis of ortho-quinols or epoxy ortho-quinols from a site-selective oxidative dearomatization process, with good yields under very mild conditions. A short total synthesis of natural product lacinilene C methyl ether is also described using this process as the key step. (Figure presented.).
Enantioselective Spirocyclopropanation of para-Quinone Methides Using Ammonium Ylides
Roiser, Lukas,Waser, Mario
supporting information, p. 2338 - 2341 (2017/05/12)
The use of Cinchona alkaloid-based chiral ammonium ylides allows for the first highly enantioselective and broadly applicable spirocyclopropanation reactions of para-quinone methides. This strategy provides a straightforward protocol toward the chiral spiro[2.5]octa-4,7-dien-6-one skeleton, which is a frequently found structural motif in important biologically active molecules.
1,6-Addition Arylation of para-Quinone Methides: An Approach to Unsymmetrical Triarylmethanes
Gao, Shang,Xu, Xiuyan,Yuan, Zhenbo,Zhou, Haipin,Yao, Hequan,Lin, Aijun
supporting information, p. 3006 - 3012 (2016/07/11)
A 1,6-addition arylation reaction of para-quinone methides with α-isocyanoacetamides and electron-rich aromatic compounds under metal-free conditions has been developed. BF3·Et2O plays two roles in the reaction: catalyzing the cyclization of α-isocyanoacetamides to give oxazoles, and activating the para-quinone methides to achieve the 1,6-addition arylation process. The reaction shows good functional group tolerance, scalability, and regioselectivity. It is a consice protocol for the synthesis of diverse unsymmetrical triarylmethanes. Further transformation of the resulting triarylmethanes provides an efficient route to some functionalized molecules.
Copper-catalyzed silylation of p-quinone methides: New entry to dibenzylic silanes
López, Aurora,Parra, Alejandro,Jarava-Barrera, Carlos,Tortosa, Mariola
, p. 17684 - 17687 (2015/12/18)
An efficient and general copper(i)-catalyzed silylation of p-quinone-methides is described. Non-symmetric dibenzylic silanes are obtained in high yields under mild reaction conditions. These compounds can be used as bench-stable benzylic carbanion precursors.
Synthesis of spiro[2.5]octa-4,7-dien-6-one with consecutive quaternary centers via 1,6-conjugate addition induced dearomatization of para-quinone methides
Gai, Kuo,Fang, Xinxin,Li, Xuanyi,Xu, Jinyi,Wu, Xiaoming,Lin, Aijun,Yao, Hequan
supporting information, p. 15831 - 15834 (2015/11/10)
An efficient one-pot approach for the synthesis of spiro[2.5]octa-4,7-dien-6-ones by employing para-quinone methides has been developed. The reaction proceeded smoothly in high yields under mild conditions without the use of metals. Moreover, all products obtained herein contained two or three consecutive quaternary centers.
Synthesis and evaluation of novel benzophenone-thiazole derivatives as potent VEGF-A inhibitors
Prashanth,Thirusangu, Prabhu,Vijay Avin,Lakshmi Ranganatha,Prabhakar,Khanum, Shaukath Ara
, p. 274 - 283 (2015/02/19)
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
Lakshmi Ranganatha,Zameer, Farhan,Meghashri,Rekha,Girish,Gurupadaswamy,Khanum, Shaukath Ara
, p. 901 - 911 (2014/01/06)
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.
