Efficient synthesis of novel 2-deoxy-C-nucleosides containing
oxa and thiadiazole derivatives and their biological activity

J 2023

Efficient synthesis of novel 2-deoxy-C-nucleosides containing oxa and thiadiazole derivatives and their biological activity

PENJARLA, Srishylam, Paidi Yella REDDY, Santhosh PENTA, Yogesh S. SANGHVI, Ludek EYER et. al.

Basic information

Original name

Efficient synthesis of novel 2-deoxy-C-nucleosides containing oxa and thiadiazole derivatives and their biological activity

Authors

PENJARLA, Srishylam, Paidi Yella REDDY, Santhosh PENTA, Yogesh S. SANGHVI, Ludek EYER, Michal STEFANIK, Daniel RŮŽEK (203 Czech Republic, belonging to the institution) and Shyamapada BANERJEE (guarantor)

Edition

Journal of Molecular Structure, Amsterdam, Elsevier, 2023, 0022-2860

Other information

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

10606 Microbiology

Country of publisher

Netherlands

Confidentiality degree

není předmětem státního či obchodního tajemství

References:

URL

Impact factor

Impact factor: 3.800 in 2022

RIV identification code

RIV/00216224:14310/23:00132638

Organization unit

Faculty of Science

DOI

http://dx.doi.org/10.1016/j.molstruc.2023.136099

UT WoS

001032754800001

Keywords in English

C -nucleoside; Oxadiazoles; Thiadiazoles; Antiviral; Antitumor; Heterocycles

Abstract

V originále

Five membered oxa- and thiadiazole derivatives have shown significant biological activity due to their unique bioisosteric properties. Herein, we describe an efficient synthetic approach leading to several novel C-nucleosides containing an oxadiazole or thiadiazole ring system. This work provides for the first-time ability to assemble & beta;-Cnucleosides in a facile manner offering an ideal framework for the possible development of new antiviral and antitumor drugs. All new C-nucleosides were tested for their activity against TBEV and SARS-CoV-2. Two of the synthesized compounds exerted mild anti-SARS-CoV-2 activity, as evidenced by the decrease in viral titers by <1 log10 PFU/ml compared with controls. Mechanism for the formation of 5-substituted 1,3,4-thiadiazole ring is proposed and a structure-activity relationship established with these C-nucleosides.

Citovat

PENJARLA, Srishylam, Paidi Yella REDDY, Santhosh PENTA, Yogesh S. SANGHVI, Ludek EYER, Michal STEFANIK, Daniel RŮŽEK and Shyamapada BANERJEE. Efficient synthesis of novel 2-deoxy-C-nucleosides containing oxa and thiadiazole derivatives and their biological activity. Journal of Molecular Structure. Amsterdam: Elsevier, 2023, vol. 1292, November 2023, p. 1-19. ISSN 0022-2860. Available from: https://dx.doi.org/10.1016/j.molstruc.2023.136099.

@article{2352604,
   author = {Penjarla, Srishylam and Reddy, Paidi Yella and Penta, Santhosh and Sanghvi, Yogesh S. and Eyer, Ludek and Stefanik, Michal and Růžek, Daniel and Banerjee, Shyamapada},
   article_location = {Amsterdam},
   article_number = {November 2023},
   doi = {http://dx.doi.org/10.1016/j.molstruc.2023.136099},
   keywords = {C -nucleoside; Oxadiazoles; Thiadiazoles; Antiviral; Antitumor; Heterocycles},
   language = {eng},
   issn = {0022-2860},
   journal = {Journal of Molecular Structure},
   title = {Efficient synthesis of novel 2-deoxy-C-nucleosides containing oxa and thiadiazole derivatives and their biological activity},
   url = {https://doi.org/10.1016/j.molstruc.2023.136099},
   volume = {1292},
   year = {2023}
}

TY  - JOUR
ID  - 2352604
AU  - Penjarla, Srishylam - Reddy, Paidi Yella - Penta, Santhosh - Sanghvi, Yogesh S. - Eyer, Ludek - Stefanik, Michal - Růžek, Daniel - Banerjee, Shyamapada
PY  - 2023
TI  - Efficient synthesis of novel 2-deoxy-C-nucleosides containing oxa and thiadiazole derivatives and their biological activity
JF  - Journal of Molecular Structure
VL  - 1292
IS  - November 2023
SP  - 1-19
EP  - 1-19
PB  - Elsevier
SN  - 00222860
KW  - C -nucleoside
KW  - Oxadiazoles
KW  - Thiadiazoles
KW  - Antiviral
KW  - Antitumor
KW  - Heterocycles
UR  - https://doi.org/10.1016/j.molstruc.2023.136099
N2  - Five membered oxa- and thiadiazole derivatives have shown significant biological activity due to their unique bioisosteric properties. Herein, we describe an efficient synthetic approach leading to several novel C-nucleosides containing an oxadiazole or thiadiazole ring system. This work provides for the first-time ability to assemble & beta;-Cnucleosides in a facile manner offering an ideal framework for the possible development of new antiviral and antitumor drugs. All new C-nucleosides were tested for their activity against TBEV and SARS-CoV-2. Two of the synthesized compounds exerted mild anti-SARS-CoV-2 activity, as evidenced by the decrease in viral titers by <1 log10 PFU/ml compared with controls. Mechanism for the formation of 5-substituted 1,3,4-thiadiazole ring is proposed and a structure-activity relationship established with these C-nucleosides.
ER  -

PENJARLA, Srishylam, Paidi Yella REDDY, Santhosh PENTA, Yogesh S. SANGHVI, Ludek EYER, Michal STEFANIK, Daniel RŮŽEK and Shyamapada BANERJEE. Efficient synthesis of novel 2-deoxy-C-nucleosides containing oxa and thiadiazole derivatives and their biological activity. \textit{Journal of Molecular Structure}. Amsterdam: Elsevier, 2023, vol.~1292, November 2023, p.~1-19. ISSN~0022-2860. Available from: https://dx.doi.org/10.1016/j.molstruc.2023.136099.

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