Rhodanine derivatives: An insight into the synthetic and medicinal perspectives as antimicrobial and antiviral agents

Abstract

Rhodanine or 2-Thioxothiazolidin-4-one is a privileged heterocyclic compound offering a wide opportunity for structural modification, lead development, and modification. It is one of the highly decorated scaffolds in the drug discovery process. Rhodanine derivatives possess a plethora of biological activities due to their ability to interact with a diverse range of protein targets, which provide tremendous opportunities to discover new drugs with different modes of action. The most common strategy for developing novel rhodanine derivatives is the introduction of structurally diverse substituents at the C-5 or N-3, or both positions. Since the inception of Epralestat into the market in 1992, the exploration of rhodanine-3acetic acids has led to the development of novel leads against different biological targets such as MRSA, HHV-6, Mycobacterial tuberculosis, dengue, etc. In the current pandemic era, some rhodanine compounds have been explored against SARS-CoV-2. In recent years, rhodanine and its derivatives have witnessed significant progress in developing new drug leads as potential antimicrobial and antiviral agents. Different synthetic methodologies and recent developments in the medicinal chemistry of rhodanine derivatives, including biological activities, their mechanistic aspects, structure-activity relationships, and in silico findings, have been compiled in the present review. This article will benefit the scientific community and offer perspectives on how these scaffolds as privileged structures might be exploited in the future for rational design and discovery of rhodaninebased bio-active molecules.

Recent Studies of Nitrogen and Sulfur Containing Heterocyclic Analogues as Novel Antidiabetic Agents: A Review

“…Rhodanine is synthesized via a component reaction of primary amines 1 , carbon disulfide, and chloroacetic acid sodium salt 98 in the presence of HCl, a faster reaction time and a larger yield of the products are achievable. Similarly, rhodanine acetic acid is synthesized via primary amines 1 , carbon disulfide chloroacetic acid sodium salt 98 , and ammino acetic acid 99 in the presence ammonium hydroxide [111] …”

“…Similarly, rhodanine acetic acid is synthesized via primary amines 1, carbon disulfide chloroacetic acid sodium salt 98, and ammino acetic acid 99 in the presence ammonium hydroxide. [111] 3.1.7.2. Pharmacological profile of rhodanine derivatives Bacha MM et al studied a range of synthetic rhodanine-3acetamide derivatives and assessed how well they inhibited aldose and aldehyde reductase.…”

Targeting phosphatase DUSP22 ameliorates skeletal muscle wasting via Akt independent JNK-FOXO3a repression

“…This compound is based on the rhodanine (2-thioxothiazolidin-4-one) chemical scaffold, which is becoming more prominent in medicine and pharmacy [42]. Rhodanine is a privileged heterocyclic compound that is amenable for structural modification and lead development, and has been classified as a highly decorated scaffold with an important position for drug development [43]. Consequently, BML-260 should be suitable for further rounds of structural optimization to improve its drug-like properties, biological stability and targeting of DUSP22.…”

Can a Small Change in the Heterocyclic Substituent Significantly Impact the Physicochemical and Biological Properties of (Z)-2-(5-Benzylidene-4-oxo-2-thioxothiazolidin-3-yl)acetic Acid Derivatives?

“…This is primarily due to the growing requirements placed on chemical compounds used, among others, in technology, pharmacy and medicine. In recent years, derivatives of rhodanine-3-acetic acid have become increasingly popular in scientific research [ 1 , 2 , 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 ]. These compounds exhibit many interesting physicochemical and biological properties, so they are being investigated for numerous applications [ 1 , 2 , 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 ].…”

“…In recent years, derivatives of rhodanine-3-acetic acid have become increasingly popular in scientific research [ 1 , 2 , 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 ]. These compounds exhibit many interesting physicochemical and biological properties, so they are being investigated for numerous applications [ 1 , 2 , 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 ]. One of them is in dye-sensitized solar cells (DSSCs) in which derivatives of rhodanine-3-acetic acid can act as dyes [ 4 , …”