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Introduction of chirality at C1 position of 1-substituted-3,4-dihydroisoquinoline by its enantioselective reduction: synthesis of chiral 1-substituted-1,2,3,4-tetrahydroisoquinoline - a review.

ABSTRACT: There is a wide range of biological activities associated with C1 chiral carbon containing 1-substituted-1,2,3,4-tetrahydroisoquinolines (1-substituted-THIQs) which constitute the isoquinoline alkaloids, a large group of natural products. This work summarizes several novel catalytic stereoselective approaches to enantioselectively reduce the 1-substituted-3,4-dihydroisoquinolines (1-substituted-DHIQs) to produce the desired 1-substituted-THIQs. The 1-substituted-DHIQs were prepared by using the Bischler-Napieralski reaction. The enantioselective reduction of 1-substituted-DHIQs was accomplished by using chiral hydride reducing agents, by hydrogenation with a chiral catalyst, by enantioselective reduction of DHIQs possessing a chiral auxiliary at the imine nitrogen by achiral metallic hydride reducing agents, or by enzymatic catalysis. Among these methods, much more work was carried out on the hydrogenation of 1-substituted-DHIQs in the presence of a chiral catalyst. This review summarizes articles and advancements on this topic from 1972 to 2023.

SUBMITTER: Asif MMA

PROVIDER: S-EPMC10077949 | biostudies-literature | 2023 Apr

REPOSITORIES: biostudies-literature

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Introduction of chirality at C1 position of 1-substituted-3,4-dihydroisoquinoline by its enantioselective reduction: synthesis of chiral 1-substituted-1,2,3,4-tetrahydroisoquinoline - a review.

Asif Md Moaz Ahmed MMA Lisa Susmita Roy SR Qais Nazmul N

RSC advances 20230406 16

There is a wide range of biological activities associated with C1 chiral carbon containing 1-substituted-1,2,3,4-tetrahydroisoquinolines (1-substituted-THIQs) which constitute the isoquinoline alkaloids, a large group of natural products. This work summarizes several novel catalytic stereoselective approaches to enantioselectively reduce the 1-substituted-3,4-dihydroisoquinolines (1-substituted-DHIQs) to produce the desired 1-substituted-THIQs. The 1-substituted-DHIQs were prepared by using the ...[more]

PMID: 37033430

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Project description:Background: Glioblastoma is the most aggressive form of brain tumors showing resistance to treatment with various chemotherapeutic agents. The most effective way to eradicate glioblastoma requires the concurrent inhibition of multiple signaling pathways and target molecules involved in the progression of glioblastoma. Recently, we obtained a series of 1,2,3,4-tetrahydroisoquinoline alkaloids with potent anti-cancer activities, including ecteinascidin-770 (ET-770; the compound 1a) and renieramycin M (RM; the compound 2a) from Thai marine invertebrates, together with a 2’-N-4”-pyridinecarbonyl derivative of ET-770 (ET-770-DR; the compound 3). We attempted to characterize the molecular pathways responsible for cytotoxic effects of these compounds on a human glioblastoma cell line U373MG. Methods: We studied the genome-wide gene expression profile on microarrays and molecular networks by using pathway analysis tools of bioinformatics. Results: All of these compounds dissolved in dimethyl sulfoxide (DMSO) as a vehicle induced apoptosis of U373MG cells at nanomolar concentrations. The compound 3 reduced the expression of 417 genes and elevated the levels of 84 genes, while ET-770 downregulated 426 genes and upregulated 45 genes. RM decreased the expression of 274 genes and increased the expression of 9 genes. The set of 196 downregulated genes and 6 upregulated genes showed an overlap among all the compounds, suggesting an existence of the common pathways involved in induction of apoptosis. We identified the ErbB (EGFR) signaling pathway as one of the common pathways enriched in the set of downregulated genes, composed of PTK2, AKT3, and GSK3B serving as key molecules that regulate cell movement and the nervous system development. Furthermore, a GSK3B-specific inhibitor induced apoptosis of U373MG cells, supporting an anti-apoptotic role of GSK3B. Conclusion: Molecular network analysis is a useful approach not only to characterize the glioma-relevant pathways but also to identify the network-based effective drug targets.

Dataset Information

Introduction of chirality at C1 position of 1-substituted-3,4-dihydroisoquinoline by its enantioselective reduction: synthesis of chiral 1-substituted-1,2,3,4-tetrahydroisoquinoline - a review.

Publications

Introduction of chirality at C1 position of 1-substituted-3,4-dihydroisoquinoline by its enantioselective reduction: synthesis of chiral 1-substituted-1,2,3,4-tetrahydroisoquinoline - a review.

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