Synthesis and anti-proliferative studies of 2-acyl-4-(het)arylthiazoles on human hepatoma cells

Rajaghatta N. Suresh; Prasanna Doddakunche Shivaramu; Toreshettahally R. Swaroop; Arunachalam Chinnathambi; Sulaiman Ali Alharbi; Chandra Sekhar Bhol; Kwang Seok Ahn; Kempegowda Mantelingu; Kanchugarakoppal S. Rangappa

doi:10.1016/j.rechem.2025.102599

Synthesis and anti-proliferative studies of 2-acyl-4-(het)arylthiazoles on human hepatoma cells

Rajaghatta N. Suresh
, Prasanna Doddakunche Shivaramu
, Toreshettahally R. Swaroop
, Arunachalam Chinnathambi
, Sulaiman Ali Alharbi
, Chandra Sekhar Bhol
, Kwang Seok Ahn
, Kempegowda Mantelingu
, Kanchugarakoppal S. Rangappa

Research output: Contribution to journal › Article › peer-review

Abstract

We herein report an improved protocol for the synthesis of 2-acyl-4-(het)arylthiazoles by reacting α-oxothioamides with α-bromocarbonyl compounds in acetonitrile under microwave irradiation. One of the thiazoles, (4-(4-bromophenyl)thiazol-2-yl)(m-tolyl)methanone (SW-07) has emerged as the best cytotoxic agent against HepG2 and HCCLM3 liver cancer cells with IC₅₀ values of 6.77 ± 1.10 μM and 7.97 ± 1.15 μM respectively. This lead compound is better than standard drug cisplatin with respect to cytotoxicity. The nuclear fragmentation, chromatin condensation and membrane blebbing enhanced the apoptotic cell death. Further, this lead compound has increased the formation of acidic vesicular organelles and thus enhanced autophagy.

Original language	English
Article number	102599
Journal	Results in Chemistry
Volume	17
DOIs	https://doi.org/10.1016/j.rechem.2025.102599
Publication status	Published - Sept 2025

Bibliographical note

Publisher Copyright:
© 2025 The Authors

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 3 Good Health and Well-being

Keywords

Anti-proliferative
Anticancer
Apoptosis
Hepatoma
Thiazoles

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10.1016/j.rechem.2025.102599

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@article{393f1b2afa0e405db92acb570ae3b8c4,

title = "Synthesis and anti-proliferative studies of 2-acyl-4-(het)arylthiazoles on human hepatoma cells",

abstract = "We herein report an improved protocol for the synthesis of 2-acyl-4-(het)arylthiazoles by reacting α-oxothioamides with α-bromocarbonyl compounds in acetonitrile under microwave irradiation. One of the thiazoles, (4-(4-bromophenyl)thiazol-2-yl)(m-tolyl)methanone (SW-07) has emerged as the best cytotoxic agent against HepG2 and HCCLM3 liver cancer cells with IC₅₀ values of 6.77 ± 1.10 μM and 7.97 ± 1.15 μM respectively. This lead compound is better than standard drug cisplatin with respect to cytotoxicity. The nuclear fragmentation, chromatin condensation and membrane blebbing enhanced the apoptotic cell death. Further, this lead compound has increased the formation of acidic vesicular organelles and thus enhanced autophagy.",

keywords = "Anti-proliferative, Anticancer, Apoptosis, Hepatoma, Thiazoles",

author = "Suresh, \{Rajaghatta N.\} and \{Doddakunche Shivaramu\}, Prasanna and Swaroop, \{Toreshettahally R.\} and Arunachalam Chinnathambi and Alharbi, \{Sulaiman Ali\} and Bhol, \{Chandra Sekhar\} and Ahn, \{Kwang Seok\} and Kempegowda Mantelingu and Rangappa, \{Kanchugarakoppal S.\}",

note = "Publisher Copyright: {\textcopyright} 2025 The Authors",

year = "2025",

month = sep,

doi = "10.1016/j.rechem.2025.102599",

language = "English",

volume = "17",

journal = "Results in Chemistry",

issn = "2211-7156",

publisher = "Elsevier BV",

}

TY - JOUR

T1 - Synthesis and anti-proliferative studies of 2-acyl-4-(het)arylthiazoles on human hepatoma cells

AU - Suresh, Rajaghatta N.

AU - Doddakunche Shivaramu, Prasanna

AU - Swaroop, Toreshettahally R.

AU - Chinnathambi, Arunachalam

AU - Alharbi, Sulaiman Ali

AU - Bhol, Chandra Sekhar

AU - Ahn, Kwang Seok

AU - Mantelingu, Kempegowda

AU - Rangappa, Kanchugarakoppal S.

PY - 2025/9

Y1 - 2025/9

N2 - We herein report an improved protocol for the synthesis of 2-acyl-4-(het)arylthiazoles by reacting α-oxothioamides with α-bromocarbonyl compounds in acetonitrile under microwave irradiation. One of the thiazoles, (4-(4-bromophenyl)thiazol-2-yl)(m-tolyl)methanone (SW-07) has emerged as the best cytotoxic agent against HepG2 and HCCLM3 liver cancer cells with IC₅₀ values of 6.77 ± 1.10 μM and 7.97 ± 1.15 μM respectively. This lead compound is better than standard drug cisplatin with respect to cytotoxicity. The nuclear fragmentation, chromatin condensation and membrane blebbing enhanced the apoptotic cell death. Further, this lead compound has increased the formation of acidic vesicular organelles and thus enhanced autophagy.

AB - We herein report an improved protocol for the synthesis of 2-acyl-4-(het)arylthiazoles by reacting α-oxothioamides with α-bromocarbonyl compounds in acetonitrile under microwave irradiation. One of the thiazoles, (4-(4-bromophenyl)thiazol-2-yl)(m-tolyl)methanone (SW-07) has emerged as the best cytotoxic agent against HepG2 and HCCLM3 liver cancer cells with IC₅₀ values of 6.77 ± 1.10 μM and 7.97 ± 1.15 μM respectively. This lead compound is better than standard drug cisplatin with respect to cytotoxicity. The nuclear fragmentation, chromatin condensation and membrane blebbing enhanced the apoptotic cell death. Further, this lead compound has increased the formation of acidic vesicular organelles and thus enhanced autophagy.

KW - Anti-proliferative

KW - Anticancer

KW - Apoptosis

KW - Hepatoma

KW - Thiazoles

UR - https://www.scopus.com/pages/publications/105013344242

U2 - 10.1016/j.rechem.2025.102599

DO - 10.1016/j.rechem.2025.102599

M3 - Article

AN - SCOPUS:105013344242

SN - 2211-7156

VL - 17

JO - Results in Chemistry

JF - Results in Chemistry

M1 - 102599

ER -

Synthesis and anti-proliferative studies of 2-acyl-4-(het)arylthiazoles on human hepatoma cells

Abstract

Bibliographical note

UN SDGs

Keywords

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