572-09-8Relevant articles and documents
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Jeanes et al.
, p. 3667,3669 (1953)
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Synthesis and biological testing of novel glucosylated epigallocatechin gallate (EGCG) derivatives
Zhang, Xin,Wang, Jing,Hu, Jiang-Miao,Huang, Ye-Wei,Wu, Xiao-Yun,Zi, Cheng-Ting,Wang, Xuan-Jun,Sheng, Jun
, (2016)
Epigallocatechin gallate (EGCG) is the most abundant component of green tea catechins and has strong physiological activities. In this study, two novel EGCG glycosides (EGCG-G1 and EGCG-G2) were chemoselectively synthesized by a chemical modification stra
Synthesis of thioglycosides by tetrathiomolybdate-mediated michael additions of masked thiolates
Sridhar, Perali Ramu,Prabhu, Kandikere Ramaiah,Chandrasekaran, Srinivasan
, p. 4809 - 4815 (2004)
An efficient one-pot methodology for the synthesis of thioglycosides in excellent yields under neutral conditions through the use of benzyltriethylammonium tetrathiomolybdate [(BnNEt3) 2MoS4; 1] as a sulfur-transfer reagent has been developed. The reagent 1 reacts with sugar halides to give sugar disulfides, which then undergo reductive cleavage in situ to provide the corresponding thiolates, followed by Michael addition to give the corresponding thioglycosides. Further, the utility of this one-pot reaction in aqueous medium has been exemplified through the use of ammonium tetrathiomolybdate [(NH4)2 MoS4; 2]. The application of this methodology has been extended to the synthesis of a variety of thiosugar analogues with excellent diastereoselectivity through inter- and intramolecular reactions. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
Structures of Nostocyclophanes A-D
Chen, Jian Lu,Moore, Richard E.,Patterson, Gregory M. L.
, p. 4360 - 4364 (1991)
Nostocyclophanes A-D are the cytotoxins associated with the blue-green alga Nostoc linckia (Roth) Bornet ex Bornet Flahault (UTEX B1932).The gross structures of these paracyclophanes have been elucidated by mass and NMR spectral analyses and the relative and absolute stereochemistry of nostocyclophane D determined by X-ray crystallography.Since the CD spectra of the four compounds are essentially identical, nostocyclophanes A-D are proposed to have the same stereochemistry.The sugar unit in nostocyclophanes A and B has been shown to be D-glucose by semisynthesis of nostocyclophane B 9-O-(2,3,4,6-tetra-O-acetyl)-β-D-glucopyranoside from nostocyclophanes B and D.
Excited-State Palladium-Catalyzed Radical Migratory Mizoroki-Heck Reaction Enables C2-Alkenylation of Carbohydrates
Liu, Peng,Mukherjee, Upasana,Ngai, Ming-Yu,Wu, Yue,Yao, Wang,Zhao, Gaoyuan,Zhou, Lin
supporting information, p. 3353 - 3359 (2022/03/08)
Excited-state palladium catalysis has emerged as a promising strategy for developing novel and valuable reactions. Herein, we report the first excited-state Pd-catalyzed 1,2-radical migratory Mizoroki-Heck reaction that enables C2-alkenylation of carbohydrates using readily available 1-bromosugars and alkenes. The reaction tolerates a wide variety of functional groups and complex molecular architectures, including derivatives of natural products and marketed drugs. Preliminary mechanistic studies and DFT calculations suggest the involvement of visible-light-induced photoexcitation of Pd species, 1,2-spin-centered-shift (SCS) process, and Heck-type cross-coupling reaction. The reaction expands the reactivity profile of excited-state Pd catalysis and provides a streamlined protocol for the preparation of a wide variety of C2-alkenylated carbohydrate mimetics to aid the discovery and development of new therapeutics, agrochemicals, and materials.
Synthesis and biological evaluation of 3β-O-neoglycosides of caudatin and its analogues as potential anticancer agents
Li, Xiao-San,Chen, Tang-Ji,Xu, Zhi-Peng,Long, Juan,He, Miao-Ying,Zhan, He-Hui,Zhuang, Hai-Cai,Wang, Qi-Lin,Liu, Li,Yang, Xue-Mei,Tang, Jin-Shan
, (2021/12/30)
In order to study the structure–activity relationship (SAR) of C21-steroidal glycosides toward human cancer cell lines and explore more potential anticancer agents, a series of 3β-O-neoglycosides of caudatin and its analogues were synthesized. The results revealed that most of peracetylated 3β-O-monoglycosides demonstrated moderate to significant antiproliferative activities against four human cancer cell lines (MCF-7, HCT-116, HeLa, and HepG2). Among them, 3β-O-(2,3,4-tri-O-acetyl-β-L-glucopyranosyl)-caudatin (2k) exhibited the highest antiproliferative activity aganist HepG2 cells with an IC50 value of 3.11 μM. Mechanical studies showed that compound 2k induced both apoptosis and cell cycle arrest at S phase in a dose dependent manner. Overall, these present findings suggested that glycosylation is a promising scaffold to improve anticancer activity for naturally occurring C21-steroidal aglycones, and compound 2k represents a potential anticancer agent deserved further investigation.
Synthesis of malformin-A1, C, a glycan, and an aglycon analog: Potential scaffolds for targeted cancer therapy
Andreana, Peter R.,Hossain, Farzana,Nishat, Sharmeen
, (2022/02/21)
Improvement in therapeutic efficacy while reducing chemotherapeutic side effects remains a vital objective in synthetic design for cancer treatment. In keeping with the ethos of therapeutic development and inspired by the Warburg effect for augmenting biological activities of the malformin family of cyclic-peptide natural products, specifically anti-tumor activity, a β-glucoside of malformin C has been designed and synthesized utilizing precise glycosylation and solution phase peptide synthesis. We optimized several glycosylation procedures utilizing different donors and acceptors. The overarching goal of this study was to ensure a targeted delivery of a glyco-malformin C analog through the coupling of D-glucose moiety; selective transport via glucose transporters (GLUTs) into tumor cells, followed by hydrolysis in the tumor microenvironment releasing the active malformin C a glycon analog. Furthermore, total synthesis of malformin C was carried out with overall improved strategies avoiding unwanted side reactions thus increasing easier purification. We also report on an improved solid phase peptide synthesis protocol for malformin A1.