Diversity Oriented Synthesis of Pyran Based Polyfunctional Stereogenic Macrocyles and Their Conformational Studies

Ajay, Arya; Sharma, Sheena; Gupt, Munna Prasad; Bajpai, Vikas; Ullah, H.; Kumar, Brijesh; Kaushik, M. P.; Konwar, Rituraj; Ampapathi, Ravi Sankar; Tripathi, Rama Pati

doi:10.1021/ol3022275

Cited by 54 publications

(23 citation statements)

References 47 publications

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“…In continuation of our interest in building a glyco‐based macrocyclic toolbox to search for modulators of protein–protein,1,2 DNA/RNA–protein3 interactions and the dissectors of signalling pathways,4 herein, we outline another strategy to obtain a different family of glycohybrids 5–10. As briefly discussed in our recent papers,11,12 the need to access compounds that bear a closer resemblance to natural products in terms of their 3D architecture and the presence of several chiral functional groups is growing constantly 13–15.…”

Section: Introductionmentioning

confidence: 99%

Building a Macrocyclic Toolbox from C‐Linked Carbohydrates Identifies Antiangiogenesis Agents from Zebrafish Assay

et al. 2013

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We report the synthesis of four different types of macrocyclic‐derived glycohybrids from carbohydrates that have an amino acid moiety in the large‐ring skeleton. These macrocyclic glycohybrids were obtained from α‐C‐1H‐ and β‐C‐1H‐linked carbohydrates. In one series, we utilized ring‐closing metathesis as the “stitching technology” to obtain two different macrocycles, i.e., trans equatorial–axial C‐1H and C‐5H and cis axial–axial C‐1H and C‐5H. The click approach was the key reaction in our second series to obtain two other macrocyclic compounds, i.e., trans equatorial–axial C‐1H and C‐5H and cis axial–axial C‐1H and C‐5H. The evaluation of this toolbox resulted in the identification of two unique compounds as antiangiogenesis agents in an embryonic zebrafish assay. Interestingly, in both cases, the macrocyclic compounds that have a cis relationship (i.e., axial–axial orientation) between C‐1H and C‐5H showed activity and their other diastereomers (i.e., equatorial–axial C‐1H and C‐5 H) with a trans relationship did not show any effect.

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Section: Introductionmentioning

confidence: 99%

Building a Macrocyclic Toolbox from C‐Linked Carbohydrates Identifies Antiangiogenesis Agents from Zebrafish Assay

et al. 2013

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“…Tripathi and co‐workers prepared structurally unique and diverse macrocyclic glycoconjugates by employing a diversity‐oriented approach based on three steps: (1) production of a polyfunctional pyran backbone, (2) formation of a 1,4‐substituted triazole substituent, and (3) formation of a 1,4,5‐trisubstituted triazole substituent. Multifunctional intermediates 121 could be derived from commercially available d ‐glucose or d ‐mannose.…”

Section: Application Of Aac Reactions For the Synthesis Of Large (mentioning

confidence: 99%

Cyclisation To Form Small, Medium and Large Rings by Use of Catalysed and Uncatalysed Azide–Alkyne Cycloadditions (AACs)

2017

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This microreview briefly summarises recent developments in cyclisation to afford small, medium and large rings (five to 30 members) by way of both catalysed and uncatalysed azide–alkyne cycloaddition (AAC). The standard AAC reactions – intramolecular Huisgen, CuAAC and RuAAC – are presented, as well as some of their contemporary variations. In addition, we present useful strategies for overcoming common problems encountered in these reactions.

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“…[6,[8][9][10][11][12][13] One of the major reasons is the lack of a wide variety of efficient synthesis methods to allow access to these compounds and their structurally related analogs in an efficient manner. [6,[8][9][10][11][12][13] One of the major reasons is the lack of a wide variety of efficient synthesis methods to allow access to these compounds and their structurally related analogs in an efficient manner.…”

Section: Introductionmentioning

confidence: 99%

An Intramolecular Heck Approach To Obtain 17‐Membered Macrocyclic Diversity and the Identification of an Antiangiogenesis Agent from a Zebrafish Assay

et al. 2013

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We report a practical and modular approach to obtain two different types of 17‐membered ring macrocyclic compounds through an intramolecular Heck reaction. These macrocyclic compounds are functionalized, that is, they contain two contiguous stereogenic hydroxy functional groups and an amino acid moiety in the macrocyclic ring skeleton. The macrocycles were then screened against a zebrafish assay to determine the antiangiogenesis activity of these small molecules. Macrocyclic compound 2.2a was identified as a potent inhibitor at 2.5 μM, whereas its acyclic precursor and the other related macrocyclic compounds did not show any effect.

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Diversity Oriented Synthesis of Pyran Based Polyfunctional Stereogenic Macrocyles and Their Conformational Studies

Abstract: A new approach to synthesize a homologous series of 14-, 15-, and 16-membered drug-like, macrocyclic glycoconjugates involving TBAHS promoted azide-propenone intramolecular cycloaddition in designed C-glycopyranosyl butenones from a simple sugar d-glucose and d-mannose is reported.

Cited by 54 publications

References 47 publications

Building a Macrocyclic Toolbox from C‐Linked Carbohydrates Identifies Antiangiogenesis Agents from Zebrafish Assay

Building a Macrocyclic Toolbox from C‐Linked Carbohydrates Identifies Antiangiogenesis Agents from Zebrafish Assay

Cyclisation To Form Small, Medium and Large Rings by Use of Catalysed and Uncatalysed Azide–Alkyne Cycloadditions (AACs)

An Intramolecular Heck Approach To Obtain 17‐Membered Macrocyclic Diversity and the Identification of an Antiangiogenesis Agent from a Zebrafish Assay

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