2038-92-8Relevant academic research and scientific papers
Synthesis of ortho-hydroxybenzophenones catalyzed by magnetically retrievable Fe3O4 nanoparticles under ligand-free conditions
Ramani, Thekkathu,Umadevi, Paspulati,Prasanth, K. Leon,Sreedhar, Bojja
, p. 6021 - 6026 (2013)
ortho-Benzoylation of phenols with aryl aldehydes to afford the substituted 2-hydroxybenzophenones can be catalyzed efficiently by Fe3O 4 nanoparticles under ligand-free conditions. This method is useful for the preparation of xanthones in good yields. The catalyst can be magnetically removed and recycled easily over four cycles without a significant decrease in activity. The applicability of magnetically retrievable Fe 3O4 nanoparticles in the oxidative coupling of aryl aldehydes with phenols under ligand free conditions is demonstrated.
Identification and optimization of biphenyl derivatives as novel tubulin inhibitors targeting colchicine-binding site overcoming multidrug resistance
Cheng, Bao,Zhu, Guirong,Meng, Linghua,Wu, Guolin,Chen, Qin,Ma, Shengming
supporting information, (2021/11/22)
Microtubule targeting agents (MTAs) are among the most successful chemotherapeutic drugs, but their efficacy is often limited by the development of multidrug resistance (MDR). Therefore, the development of novel MTAs with the ability to overcome MDR is urgently needed. In this contribution, through modification of the unsymmetric biaryl compounds, we discovered a novel compound dxy-1-175 with potent anti-proliferative activity against cancer cells. Mechanistic study revealed that dxy-1-175 inhibited tubulin polymerization by interacting with the colchicine-binding site of tubulin, which caused cell cycle arrest at G2/M phase. Based on the predicted binding model of dxy-1-175 with tubulin, a series of new 4-benzoylbiphenyl analogues were designed and synthesized. Among them, the hydrochloride compound 12e with improved solubility and good stability in human liver microsome, exhibited the most potent anti-proliferative activity with IC50 value in the low nanomolar range, and markedly inhibited the growth of breast cancer 4T1 xenograft in vivo. Notably, 12e effectively overcame P-gp-mediated MDR and our preliminary data suggested that 12e may not be a substrate of P-glycoprotein (P-gp). Taken together, our study reveals a novel MTA 12e targeting the colchicine-binding site with potent anticancer activity and the ability to circumvent MDR.
Cu/Ag mediated peroxide-free synthesis of benzoylated naphthol derivatives
Prasanna Kumari, Subramaniyan,Suresh, Pavithira,Muthukumar, Vijayashree,Selva Ganesan, Subramaniapillai
supporting information, (2020/10/13)
A peroxide-free methodology was developed for the synthesis of benzoylated naphthol/phenol derivatives through oxidative deamination reaction performed under aerobic reaction conditions. A synergistic combination of Cu(OTf)2 and Ag2O was used to convert the aminonaphthols and aminophenols to the corresponding benzoylated derivatives. The definite role of atmospheric oxygen to assist the reaction was proved by performing the reaction in the argon atmosphere.
Rhodium-Catalyzed Directing-Group-Assisted Aldehydic C–H Arylations with Aryl Halides
Rao, Maddali L. N.,Ramakrishna, Boddu S.
, p. 5080 - 5093 (2017/09/20)
A rhodium-catalyzed general protocol for the directing-group-assisted arylation of aromatic aldehydic C–H bonds was developed. This method involves either hydroxy- or amino-group-directed aldehyde C–H arylation with various aryl halides. A broad synthetic scope for the preparation of 2-hydroxybenzophenones was established with electronically variant salicylaldehydes and aryl halides with chemo- and regioselective possibilities. The developed protocol was also applied in the synthesis of medicinally important 3-salicyloylpyridines in high yields.
Iridium- and rhodium-catalyzed C-H activation and formyl arylation of benzaldehydes under chelation-assistance
Yang, Xifa,Wang, He,Zhou, Xukai,Li, Xingwei
supporting information, p. 5233 - 5237 (2016/07/06)
Mild and efficient synthesis of benzophenones via Ir(iii)- and Rh(iii)-catalyzed, directing group-assisted formyl C-H arylation of benzaldehydes has been achieved using diaryliodonium salts, in which Rh(iii) and Ir(iii) catalysts exhibited a complementary
Rh(III)-catalyzed aldehyde C-H bond functionalization of salicylaldehydes with arylboronic acids
Wang, Dahai,Cui, Sunliang
, p. 8511 - 8516 (2016/01/25)
A Rh(III)-catalyzed aldehyde C-H bond functionalization of salicylaldehydes with arylboronic acids has been developed, with features of mild reaction condition and high efficiency. Furthermore, the functionalized 2-hydroxybenzophenone could be subject to divergent synthesis of heterocycles.
Preparation of benzoyloxy benzophenone derivatives and their inhibitory effects of ICAM-1 expression
Kwon, Eun Mi,Kim, Cheol Gi,Goh, Ah Ra,Park, Jinseu,Jun, Jong-Gab
, p. 1939 - 1944 (2012/08/07)
Benzoyloxy benzophenone derivatives were prepared in 3 steps including DCC coupling, Fries rearrangement and esterification from benzoic acids in 24-89% total yields. Among the prepared 12 benzophenone analogues 1a-1l, the compound 1b having three chloro groups at the para position showed maximum inhibitory effects of ICAM-1 expression but, 1a which have no substituents at all showed no inhibitory activity. This study provides the evidences that benzoyloxy benzophenone derivative, 1b may exert its anti-inflammatory activity by suppressing IFN-γ-induced ICAM-1 expression.
Rearrangement of 2-aryloxybenzaldehydes to 2-hydroxybenzophenones by rhodium-catalyzed cleavage of aryloxy C-O bonds
Rao, Honghua,Li, Chao-Jun
supporting information; experimental part, p. 8936 - 8939 (2011/11/07)
Lost in the shuffle: An unprecedented rearrangement of the title compounds proceeds by the simultaneous rhodium-catalyzed cleavage of aryloxy C-O and aldehyde C-H bonds (see scheme). The reaction tolerates the presence of various catalytically reactive substituents such as aryl halides, nitrile, and esters.
