Stereoselective synthesis of natural product inspired carbohydrate fused pyrano[3,2-c]quinolones as antiproliferative agents

2018 ◽  
Vol 16 (12) ◽  
pp. 2049-2059 ◽  
Author(s):  
Priti Kumari ◽  
Chintam Narayana ◽  
Shraddha Dubey ◽  
Ashish Gupta ◽  
Ram Sagar
Keyword(s):  
Anticancer Activity ◽  
Natural Product ◽  
Stereoselective Synthesis ◽  
Efficient Synthesis ◽  
Antiproliferative Agents ◽  
Quinolone Derivatives

Design and efficient synthesis of new carbohydrate fused pyrano[3,2-c]quinolone derivatives and their submicromolar anticancer activity.

scholarly journals Correction: Stereoselective synthesis of natural product inspired carbohydrate fused pyrano[3,2-c]quinolones as antiproliferative agents

2018 ◽  
Vol 16 (12) ◽  
pp. 2185-2185 ◽  
Author(s):  
Priti Kumari ◽  
Chintam Narayana ◽  
Shraddha Dubey ◽  
Ashish Gupta ◽  
Ram Sagar
Keyword(s):  
Natural Product ◽  
Stereoselective Synthesis ◽  
Antiproliferative Agents

Correction for ‘Stereoselective synthesis of natural product inspired carbohydrate fused pyrano[3,2-c]quinolones as antiproliferative agents’ by Priti Kumari et al., Org. Biomol. Chem., 2018, DOI: 10.1039/c7ob03186f.

Stereoselective Synthesis of Pyroglutamate Natural Product Analogs from α- Aminoacids and their Anti-Cancer Evaluation

2013 ◽  
Vol 13 (10) ◽  
pp. 1514-1530 ◽  
Author(s):  
Srinivas Tekkam ◽  
Mohammad Alam ◽  
Matthew Just ◽  
Steven Berry ◽  
Joseph Johnson ◽  
...  
Keyword(s):  
Natural Product ◽  
Stereoselective Synthesis ◽  
Anti Cancer

scholarly journals Stereoselective Synthesis of the Di-Spirooxindole Analogs Based Oxindole and Cyclohexanone Moieties as Potential Anticancer Agents

Molecules ◽  
2021 ◽  
Vol 26 (20) ◽  
pp. 6305
Author(s):  
Abdullah Mohammed Al-Majid ◽  
M. Ali ◽  
Mohammad Shahidul Islam ◽  
Saeed Alshahrani ◽  
Abdullah Saleh Alamary ◽  
...  
Keyword(s):  
Anticancer Activity ◽  
Cell Line ◽  
Cell Lines ◽  
Cancer Cell ◽  
Anticancer Agents ◽  
Stereoselective Synthesis ◽  
Cancer Cell Lines ◽  
Azomethine Ylides ◽  
Active Member ◽  
One Pot

A new series of di-spirooxindole analogs, engrafted with oxindole and cyclohexanone moieties, were synthesized. Initially, azomethine ylides were generated via reaction of the substituted isatins 3a–f (isatin, 3a, 6-chloroisatin, 3b, 5-fluoroisatin, 3c, 5-nitroisatin, 3d, 5-methoxyisatin, 3e, and 5-methylisatin, 3f, and (2S)-octahydro-1H-indole-2-carboxylic acid 2, in situ azomethine ylides reacted with the cyclohexanone based-chalcone 1a–f to afford the target di-spirooxindole compounds 4a–n. This one-pot method provided diverse structurally complex molecules, with biologically relevant spirocycles in a good yields. All synthesized di-spirooxindole analogs, engrafted with oxindole and cyclohexanone moieties, were evaluated for their anticancer activity against four cancer cell lines, including prostate PC3, cervical HeLa, and breast (MCF-7, and MDA-MB231) cancer cell lines. The cytotoxicity of these di-spirooxindole analogs was also examined against human fibroblast BJ cell lines, and they appeared to be non-cytotoxic. Compound 4b was identified as the most active member of this series against prostate cancer cell line PC3 (IC50 = 3.7 ± 1.0 µM). The cyclohexanone engrafted di-spirooxindole analogs 4a and 4l (IC50 = 7.1 ± 0.2, and 7.2 ± 0.5 µM, respectively) were active against HeLa cancer cells, whereas NO2 substituted isatin ring and meta-fluoro-substituted (2E,6E)-2,6-dibenzylidenecyclohexanone containing 4i (IC50 = 7.63 ± 0.08 µM) appeared to be a promising agent against the triple negative breast cancer MDA-MB231 cell line. To explore the plausible mechanism of anticancer activity of di-spirooxindole analogs, molecular docking studies were investigated which suggested that spirooxindole analogs potentially inhibit the activity of MDM2.

scholarly journals Palladium(II)-Catalyzed Efficient Synthesis of Wedelolactone and Evaluation as Potential Tyrosinase Inhibitor

Molecules ◽  
2019 ◽  
Vol 24 (22) ◽  
pp. 4130
Author(s):  
Huidan Huang ◽  
Jianqiu Chen ◽  
Jie Ren ◽  
Chaofeng Zhang ◽  
Fei Ji
Keyword(s):  
Natural Product ◽  
Raw Material ◽  
Coupling Reactions ◽  
Biosynthesis Pathway ◽  
Tyrosinase Inhibitor ◽  
Efficient Synthesis ◽  
Melanin Biosynthesis ◽  
Methodological Research ◽  
Palladium Catalyzed ◽  
Tyrosinase Inhibitors

Tyrosinase is an enzyme widely distributed in nature, which has multiple functions, especially in the melanin biosynthesis pathway. Despite the few clinically available tyrosinase inhibitors for whitening, a great demand remains for novel compounds with low side effects in terms of potential carcinogenicity and improved clinical efficacy. A natural product, wedelolactone (WEL), with a polyhydroxyl moiety, attracted our attention as a potential tyrosinase inhibitor. Before we studied the biological activity of the natural product, a synthetic methodological research was firstly carried to obtain enough raw material. WEL could be obtained efficiently through palladium-catalyzed boronation/coupling reactions and 2,3-dicyano-5,6-dichlorobenzoquinone (DDQ)-involved oxidative deprotection/annulation reactions. Immediately after, the natural product was proven to be an efficient tyrosinase inhibitor. In conclusion, we developed a mild and efficient approach for the preparation of WEL, and the natural product was disclosed to have anti-tyrosinase activity, which could be widely used in multiple fields.

scholarly journals Efficient synthesis of α-alkyl-β-amino amides by transaminase-mediated dynamic kinetic resolutions

2019 ◽  
Vol 9 (15) ◽  
pp. 4083-4090 ◽  
Author(s):  
Ángela Mourelle-Insua ◽  
Daniel Méndez-Sánchez ◽  
James L. Galman ◽  
Iustina Slabu ◽  
Nicholas J. Turner ◽  
...  
Keyword(s):  
Kinetic Resolution ◽  
Stereoselective Synthesis ◽  
Efficient Synthesis ◽  
Dynamic Kinetic Resolution ◽  
Amino Amides ◽  
Kinetic Resolutions

A transaminase-catalyzed dynamic kinetic resolution is described for the stereoselective synthesis of a series of α-alkyl-β-amino amides.

scholarly journals Unexpected isocyanide-based three-component bicyclization for the stereoselective synthesis of densely functionalized pyrano[3,4-c]pyrroles

2016 ◽  
Vol 52 (5) ◽  
pp. 900-903 ◽  
Author(s):  
Qian Gao ◽  
Wen-Juan Hao ◽  
Feng Liu ◽  
Shu-Jiang Tu ◽  
Shu-Liang Wang ◽  
...  
Keyword(s):  
Stereoselective Synthesis ◽  
Efficient Synthesis ◽  
Dialkyl Acetylenedicarboxylates

A novel three-component bicyclization strategy for the efficient synthesis of densely functionalized pyrano[3,4-c]pyrroles has been established from readily accessible 3-aroylacrylic acids, dialkyl acetylenedicarboxylates and isocyanides.

scholarly journals Novel 11-Substituted Ellipticines as Potent Anticancer Agents with Divergent Activity against Cancer Cells

2019 ◽  
Vol 12 (2) ◽  
pp. 90 ◽  
Author(s):  
Charlotte M. Miller ◽  
Elaine C. O’Sullivan ◽  
Florence O. McCarthy
Keyword(s):  
Anticancer Activity ◽  
Cancer Cells ◽  
Natural Product ◽  
Anticancer Agents ◽  
Cellular Growth ◽  
Growth Effects

Ellipticines have well documented anticancer activity, in particular with substitution at the 1-, 2-, 6- and 9-positions. However, due to limitations in synthesis and coherent screening methodology the full SAR profile of this anticancer class has not yet been achieved. In order to address this shortfall, we have set out to explore the anticancer activity of this potent natural product by substitution. We currently describe the synthesis of novel 11-substituted ellipticines with two specific derivatives showing potency and diverging cellular growth effects.

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