Article
Biochemistry & Molecular Biology
Yi-Lin He, Miao Zhong, Zi-Long Song, Yu-Kai Shen, Lanning Zhao, Jianguo Fang
Summary: This study reports the design and synthesis of a series of Baylis-Hillman adducts, among which a typical adduct showed superior cytotoxicity against HepG2 cells. The selected typical adduct was found to selectively target TrxR in HepG2 cells, leading to the disruption of intracellular redox homeostasis. It also arrested the cell cycle and significantly restrained the metastasis of HepG2 cells. These findings suggest that the selected typical adduct, as well as other Baylis-Hillman skeleton-bearing compounds, hold promise as candidate or ancillary agents for the treatment of various cancers.
BIOORGANIC & MEDICINAL CHEMISTRY
(2023)
Article
Chemistry, Organic
Dongqiu Li, Fang Cheng, Yuhai Tang, Jing Li, Yang Li, Jiao Jiao, Silong Xu
Summary: In this study, we describe a DABCO-catalyzed [4 + 2] annulation reaction between 5-methylenehex-2-ynedioates and electron-deficient olefins, which leads to the formation of functionalized cyclohexadienes in good yields under mild reaction conditions. The incorporation of the beta- and epsilon-carbons of the substrates for C-C bond formation represents a novel reactivity different from previous reports. It is believed that the annulation proceeds through a domino cyclization initiated by a cross Rauhut-Currier reaction.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Dipak J. J. Dahatonde, Aritra Ghosh, Adilakshmi Vutla, Sanjay Batra
Summary: In this study, a regioselective one-pot synthesis of 1,4,5-trisubstituted pyrazoles was reported using Morita-Baylis-Hillman (MBH) acetates derived from aryl aldehydes and alkyl or aryl hydrazines in the presence of iodine under aerobic conditions. The reaction involved nucleophilic substitution, oxidation, intramolecular aza-Michael reaction, cyclization, and oxidative aromatization. The synthetic applications of the pyrazoles in various reactions were also demonstrated.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Parasitology
Ana Carolina Santana Vieira, Mariana da Silva Santos, Anderson Brandao Leite, Amanda Evelyn da Silva, Luiz Henrique Agra Cavalcante-Silva, Gabrielle de Souza Augusto Pereira, Sany Delany Gomes Marques, Barbara Viviana de Oliveira Santos, Alysson Wagner Fernandes Duarte, Aline Cavalcante de Queiroz, Kristerson Reinaldo de Luna-Freire, Magna Suzana Alexandre-Moreira
Summary: Leishmaniasis is a neglected disease with limited treatment options and adverse effects. This study evaluated the antileishmanial activity of several derivatives and found that one derivative (1G) showed activity against both promastigote and amastigote forms with low toxicity to macrophages.
PARASITOLOGY RESEARCH
(2022)
Article
Chemistry, Physical
Yinuo Li, Cuiyu Bao, Zhoutong Sun, Wuyuan Zhang, Bo Yuan
Summary: The oxidation of benzylic alcohols coupled with the Morita-Baylis-Hillman (MBH) reactions in biocatalytic compatible conditions was evaluated. One-pot cascades were described and compared, including a chemoenzymatic cascade with galactose oxidase (GOase M3-5) and 1,4-Diazabicyclo [2.2.2] octane (DABCO), a concurrent dual-enzyme cascade with GOase M3-5 and a computationally designed enzyme MBHase (BH32.14), and a whole cell biotransformation with co-expression modules of the two enzymes. The cascades showed high conversions and yields, with some products having high optical purity.
Article
Chemistry, Organic
Xian-Zhou Zheng, Kai Chen, Jun-An Xiao, Jun Li, Sha-Sha Wang, Qing-Lan Zhao, Hao-Yue Xiang, Xiao-Qing Chen, Hua Yang
Summary: In a newly developed palladium-catalysed enantioselective nucleophilic substitution reaction, an unusual temperature-enantioselectivity relationship was observed where higher enantioselectivity was achieved at an abnormally high temperature (140 degrees C) in less than 5 minutes. Experimental and computational studies suggest that temperature-dependent changes in the rate-determining steps may be responsible for the abnormal effect of temperature on stereocontrol in this process.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Niannian Ni, Jiawei Chen, Siyu Ding, Dongping Cheng, Xiaonian Li, Xiaoliang Xu
Summary: The Ru-catalyzed coupling reaction of Morita-Baylis-Hillman (MBH) adducts with tertiary amines and alpha-trimethylsilyl amines under visible light showed different chemical reaction characteristics when compared to MBH adducts with ester groups as withdrawing-electron groups. The universality of substrates has been extended, allowing for the synthesis of structurally complementary acrylonitriles in satisfied yields under mild conditions and providing an opportunity to discover new meaningful bioactive compounds.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Yuanyuan Ren, Ransong Ma, Yang Feng, Ke-Hu Wang, Junjiao Wang, Danfeng Huang, Xiaobo Lv, Yulai Hu
Summary: Difluoroacetohydrazonoyl bromides are stable in air and can be used as good difluoromethyl building blocks for the construction of CF2H-substituted pyrazoline and pyrazole compounds through [3+2] cycloaddition with electron-deficient olefins under mild conditions. The method offers mild reaction conditions, good regioselectivity, broad substrate scopes, and easy operation.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
S. Banuprakash Goud, Soumitra Guin, Meher Prakash, Sampak Samanta
Summary: A novel synthetic method for the preparation of highly substituted biologically relevant 2-aminonicotinonitriles with satisfactory yields is reported. This method involves creating two new C-N bonds under mild conditions and is applicable to gram-scale syntheses with excellent functional group tolerance.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Bartosz Bieszczad, Samir Z. Zard
Summary: A versatile strategy for alpha-substitution of enones has been developed using alpha-xanthyl-beta-hydroxy ketones as synthetic equivalents of alkenyl radicals, allowing for one-pot reactions and extension to alpha,beta-unsaturated esters in some cases.
Article
Chemistry, Organic
Lenin Dandamudi, Payal Malvi
Summary: A simple and efficient method for synthesizing (E)-5-arylylidene-3-((substituted-ind-2-en-1-one)methyl)-3-aryl piperidine-2,6-diones from Baylis-Hillman acetates is described. This involves bis-alkylation of aryl acetonitriles followed by a facile domino bis-cyclization reaction involving C-C and C-N bond formations.
Article
Chemistry, Organic
He Zhao, Niannian Ni, Xiaonian Li, Dongping Cheng, Xiaoliang Xu
Summary: The preparation of N-containing alpha,beta-unsaturated carboxylate derivatives from alpha-silylamine and Baylis-Hillman adducts under visible light irradiation was reported. The formation of alpha-aminoalkyl radical is regioselective compared with the previous reports. The reaction was successfully performed without additional additives under mild conditions.
TETRAHEDRON LETTERS
(2021)
Review
Chemistry, Organic
Nitisha Chakraborty, Amrit Krishna Mitra
Summary: DABCO is a versatile and environmentally friendly organocatalyst that has attracted a lot of attention in the field of organic transformations. It acts as both a nucleophile and a base, enabling the synthesis of a wide range of molecules and functional groups. Its applications in various reactions, such as cycloaddition, coupling, nucleophilic substitution, and oxidation, are also noteworthy.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Xiang-Hong He, Xue-Ju Fu, Gu Zhan, Nan Zhang, Xiang Li, Hong-Ping Zhu, Cheng Peng, Gu He, Bo Han
Summary: This study describes an organocatalytic asymmetric [3+3] annulation reaction using isatin-derived MBH carbonates and indolin-2-imines. The reaction provides a novel enantioselective approach for the synthesis of multifunctionalized alpha-carboline-spirooxindole hybrids with high yields and stereoselectivities. The synthesized compounds exhibit significant inhibition of proliferation in colorectal cancer cell lines, and the most potent compound activates autophagy and cytoprotective autophagy in HCT116 cells.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Engineering, Chemical
Temitope O. Olomola, Solomon S. Durodola, Lukman O. Olasunkanmi, Abolanle S. Adekunle
Summary: Two 3-chloromethylcoumarins synthesized via the Baylis-Hillman reaction were found to effectively inhibit the corrosion of mild steel in concentrated hydrochloric acid. The inhibition efficiency increased with increasing concentration of the 3-chloromethylcoumarins. Among the two compounds, 3-chloromethyl-8-ethoxycoumarin exhibited higher inhibition efficiency than 6-chloro-3-chloromethylcoumarin, especially at low concentrations and temperatures.
JOURNAL OF ADHESION SCIENCE AND TECHNOLOGY
(2022)
Article
Chemistry, Organic
Geeta Devi Yadav, Pooja Chaudhary, Balaram Pani, Surendra Singh
Summary: Chiral transition metal complexes with privileged ligands are efficient catalysts for various asymmetric organic transformations. Transition metal complexes of C1-symmetric pyrrolidine-based ligands have been widely used in asymmetric organic reactions. However, a comprehensive review article on the transition metal complexes of chiral C1-symmetric pyrrolidine-based ligands derived from (L)-proline has not been published.
TETRAHEDRON LETTERS
(2024)
