1457-46-1Relevant academic research and scientific papers
A New Synthesis Strategy for Rhodanine and Its Derivatives
Pan, Zhenliang,An, Wankai,Wu, Lulu,Fan, Liangxin,Yang, Guoyu,Xu, Cuilian
, p. 1131 - 1134 (2021/05/25)
Rhodanine and its derivatives have been known as privileged structures in pharmacological research because of their wide spectrum of biological activities, but the synthesis method of rhodanine skeleton is limited. In this paper, not only rhodanine skeleton, but also N -aryl rhodanines can be directly prepared via the reaction of thioureas and thioglycolic acid in one step catalyzed by protic acid, which provides a new approach of the synthesis of rhodanine and its derivatives. The developed strategy is straightforward, efficient, atom economical, and convenient in good yields.
Design, synthesis and biological evaluation of imidazolidine-2,4-dione and 2-thioxothiazolidin-4-one derivatives as lymphoid-specific tyrosine phosphatase inhibitors
Liang, Xiao,Fu, Huansheng,Xiao, Peng,Fang, Hao,Hou, Xuben
, (2020/08/06)
Lymphoid-specific tyrosine phosphatase (LYP), which exclusively exists in immune cells and down-regulates T cell receptor signaling (TCR), has becoming a potent target for various autoimmune diseases. Herein, we designed and synthesized imidazolidine-2,4-dione and 2-thioxothiazolidin-4-one derivatives as new LYP inhibitors. Among them, the cinnamic acids-based inhibitors (9p and 9r) displayed good LYP inhibitory activities (IC50 = 2.85–6.95 μM). Especially, the most potent inhibitor 9r was identified as competitive inhibitor (Ki = 1.09 μM) and bind LYP reversibly. Meanwhile, 9r exhibited better selectivity over other phosphatases than known LYP inhibitor A15. Furthermore, compound 9r could regulate TCR associated signaling pathway in Jurkat T cell.
Compound with piperine skeleton structure as well as preparation and application thereof
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Paragraph 0044; 0051-0053, (2020/07/02)
The invention discloses a compound with a piperine skeleton structure as well as preparation and application of the compound, wherein the structural formulas of the compound are shown as a formula I-1and a formula I-2; in the formulas, R1 is hydrogen, halogen, nitryl or cyano, or substituted or unsubstituted hydroxyl, amino, carboxyl, ester group, hydrosulfenyl, acylamino, ureido, C1-C5 straight-chain or branched-chain alkyl and C1-C5 alkoxy; R2 is hydrogen, halogen, nitro or cyano, or substituted or unsubstituted hydroxyl, amino, carboxyl, ester group, hydrosulfenyl, acylamino, ureido, phenyl, aryl and aromatic heterocyclic group, or substituted or unsubstituted C1-C5 straight-chain or branched-chain alkyl, or substituted or unsubstituted C1-C5 alkoxy, or substituted or unsubstituted C6-C30 aryl, fused ring and fused heterocyclic ring. As a chitinase inhibitor, the compound provided by the invention has the advantages of high activity, good broad spectrum and easiness in synthesis, and shows excellent insecticidal ability and insecticidal spectrum.
Synthesis and Biological Evaluation of Novel Carbazole Hybrids as Promising Antimicrobial Agents
Shaikh, Mahamadhanif S.,Chandrasekaran, Balakumar,Palkar, Mahesh B.,Kanhed, Ashish M.,Kajee, Afsana,Mlisana, Koleka P.,Singh, Parvesh,Ghai, Meenu,Cleopus Mahlalela, Mavela,Karpoormath, Rajshekhar
, (2020/04/23)
Two series of carbazole analogs of 8-methoxy-N-substituted-9H-carbazole-3-carboxamides (series 1) and carbazolyl substituted rhodanines (series 2) were synthesized through facile synthetic routes. All the final compounds from these two series were evaluated for their preliminary in vitro antifungal and antibacterial activity against four fungal (Candida albicans, Cryptococcus neoformans, Cryptococcus tropicalis and Aspergillus niger) and four bacterial (Staphylococcus aureus, Bacillus subtilis, Escherichia coli and Pseudomonas aeruginosa) strains, respectively. Among the tested compounds, three compounds of series 1 displayed promising antifungal and antibacterial activity, especially against C. neoformans and S. aureus. In addition, one compound of series 1 displayed notable antimicrobial activity (MIC: 6.25 μg/mL) against clinical isolates of C. albicans and C. neoformans (MIC: 12.5 μg/mL). From the second series, four compounds exhibited significant antifungal and antibacterial activity, especially against C. neoformans and S. aureus. The most active compound of series 2 displayed a prominent antimicrobial activity against C. neoformans (MIC: 3.125 μg/mL) and S. aureus (MIC: 1.56 μg/mL), respectively.
Synthesis, characterization, antibacterial and antioxidant potency of nsubstituted- 2-sulfanylidene-1,3-thiazolidin-4-one derivatives and QSAR study
Brahmbhatt, Harshad,Molnar, Maja,Pavi?, Valentina,Rastija, Vesna
, p. 840 - 849 (2020/01/25)
Background: Rhodanine is known for its potential and important role in the medicinal chemistry since its derivatives exhibit a wide range of pharmacological activities such as antibacterial, antifungal, antidiabetic, antitubercular, anti-HIV, antiparasitic, antioxidant, anticancer, antiproliferative and anthelmintic agents. Objectives: Since N-substituted rhodanine synthons are rarely commercially available, it is desirable to develop a straightforward synthetic approach for the synthesis of these key building blocks. The objective was to synthesize a series of rhodanine derivatives and to investigate their antimicrobial and antioxidant activity. Also, in order to obtain an insight into their structure-activity relationship, QSAR studies on the antioxidant activity were performed. Methods: 1H and 13C FTNMR spectra were recorded on Bruker Avance 600 MHz NMR Spectrometer, mass analysis was carried out on ESI+ mode by LC-MS/MS API 2000. 2,2-Diphenyl-1- picrylhydrazyl radical scavenging activity (% DPPH) was determined in dimethylsulfoxide (DMSO) as a solvent. The antibacterial activity was assessed against Bacillus subtilis, Staphylococcus aureus (Gram positive) and Escherichia coli, Pseudomonas aeruginosa (Gram negative) bacteria in terms of the minimum inhibitory concentrations (MICs) by a modified broth microdilution method. Results: A series of N-substituted-2-sulfanylidene-1,3-thiazolidin-4-ones were synthesized and characterized by 1H NMR, 13C NMR, FTIR, GC MS, LCMS/MS and C,H,N,S elemental analysis. Most of the synthesized compounds showed moderate to excellent antibacterial activity (MIC values from 125 μg/ml to 15.62 μg/mL) and DPPH scavenging activity (from 3.60% to 94.40%). Compound 2-thioxo-3- (4-(trifluoromethyl)-phenyl)thiazolidin-4-one showed the most potent activity against Escherichia coli (3.125 μg/mL), equivalent to antibiotic Amikacin sulphate and against Staphylococcus aureus (0.097 μg/ml), 100 times superior then antibiotic Amikacin sulphate. It has also shown a potent antioxidant activity (95% DPPH scavenging). Two best QSAR models, obtained by GETAWAY descriptor R7p+, Balabans molecular connectivity topological index and Narumi harmonic topological index (HNar), suggest that the enhanced antioxidant activity is related to the presence of pairs of atoms higher polarizability at the topological distance 7, substituted benzene ring and longer saturated aliphatic chain in N-substituents. Conclusion: A series of novel N-substituted-2-thioxothiazolidin-4-one derivatives were designed, synthesized, characterized and evaluated for their antibacterial and antioxidant activity in vitro. Majority of the compounds showed excellent antibacterial activity compared to ampicillin and few of them have an excellent activity as compared to Chloramphenicol standard antibacterial drug. The QSAR study has clarified the importance of presenting a pairs of atoms higher polarizability, such as Cl and S at the specific distance, as well as the substituted benzene ring and a long saturated aliphatic chain in N-substituents for the enhanced antioxidant activity of 2-sulfanylidene-1,3- thiazolidin-4-one derivatives.
Synthesis of 5-substituted 2-ylidene-1,3-thiazolidin-4-one derivatives and evaluation of their anticancer and antioxidant activities
Saied, Khaled F.,Kandeel, Kamal A.,Abdelwahab, Salwa S.,Ahmed, Osama M.
, p. 993 - 1003 (2019/11/16)
[Figure not available: see fulltext.] Novel 5-(aroyl)methyl- and 5-(aroyl)methylen-2-ylidene-1,3-thiazolidin-4-ones have been prepared in high yields using ketene N,S-acetal salts, obtained from phenyl isothiocyanate and propanedinitrile or ethyl cyanoacetate. Several of the newly synthesized 1,3-thiazolidin-4-one derivatives demonstrate high antioxidant and anticancer activities.
Discovery of novel N-methyl carbazole tethered rhodanine derivatives as direct inhibitors of Mycobacterium tuberculosis InhA
Shaikh, Mahamadhanif S.,Kanhed, Ashish M.,Chandrasekaran, Balakumar,Palkar, Mahesh B.,Agrawal, Nikhil,Lherbet, Christian,Hampannavar, Girish A.,Karpoormath, Rajshekhar
supporting information, p. 2338 - 2344 (2019/06/20)
InhA (Enoyl-ACP reductase) plays a crucial role in the biosynthetic pathway of cell wall synthesis in Mycobacterium tuberculosis (Mtb). Isoniazid (INH) is an important first-line drug, which inhibits InhA. The rapid increase in resistance to INH and currently marketed drugs as well as emergence of MDR-TB and XDR-TB has complicated the diagnosis and treatment of Mtb with ever increasing threat to human kind. Herein, we report novel N-methyl carbazole derivatives as potential anti-TB compounds acting directly via InhA inhibition. All the synthesized final compounds were screened against Mtb virulent cell line H37Rv and investigated the InhA enzyme inhibition. Interestingly, compound 9e displayed promising inhibition (91%) at 50 μM concentration and IC50 of 2.82 μM against InhA. To understand the ligand receptor interaction between compound 9e and InhA, molecular docking and molecular dynamics experiments were performed. The computational results were in agreement with the observed experimental data. Further, the cytotoxicity studies on mammalian cells revealed that all the compounds were safe.
Unexpected Synthesis of 2,3,5,6-Tetrahydro-1H-pyrrolo[3,4-c]pyridine-1,3,6-triones by a Double Michael Addition/CS2 Extrusion/Double Cyclization Sequence
Mari, Giacomo,De Crescentini, Lucia,Favi, Gianfranco,Santeusanio, Stefania,Lillini, Samuele,Mantellini, Fabio
, p. 6291 - 6298 (2017/11/21)
Bis adducts derived from a double Michael addition of rhodanine to an azo-ene system of two molecules of 1,2-diaza-1,3-dienes (DDs) have furnished the corresponding 2,3,5,6-tetrahydro-1H-pyrrolo[3,4-c]pyridine-1,3,6-triones by means of a CS2 extrusion/double cyclization sequence. The incorporation of two units (4 and 2 atoms) of DDs into the fused bicyclic heterocycles represents a new application of this versatile class of molecules in heterocyclic synthesis.
3. 5 - disubstituted the rhodanine class anti-withers apoptotic protein Bcl - 2 inhibitor and preparation method and application
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Paragraph 0106-0107, (2017/08/25)
The invention discloses a 3,5-disubstituted rhodanine anti-apoptosis protein Bc1-2 inhibitor as well as preparation method and an application thereof. The compound has a structure of a general formula I. The compound disclosed by the invention has high inhibitory activity on Bc1-2 and can be used for preparation of medicines for preventing or treating related mammal diseases caused by abnormal expression of anti-apoptosis protein Bc1-2. The invention also relates to a pharmaceutical application of a composition of the compound with the structure of the general formula I. The structural formula is as shown in the specification.
Synthesis and biological evaluation of new rhodanine analogues bearing 2-chloroquinoline and benzo[h]quinoline scaffolds as anticancer agents
Ramesh, Vadla,Ananda Rao, Boddu,Sharma, Pankaj,Swarna,Thummuri, Dinesh,Srinivas, Kolupula,Naidu,Jayathirtha Rao, Vaidya
, p. 569 - 580 (2014/07/21)
Several rhodanine derivatives (9-39) were synthesized for evaluation of their potential as anticancer agents. Villsmeier cyclization to synthesize aza-aromatic aldehydes, rhodanine derivatives preparation and Knoevenagel type of condensation between the rhodanines and aza-aromatic aldehydes are key steps used for the synthesis of 31 compounds. In vitro antiproliferative activity of the synthesized rhodanine derivatives (9-39) was studied on a panel of six human tumor cell lines viz. HGC, MNK-74, MCF-7, MDAMB-231, DU-145 and PC-3 cell lines. Some of the compounds were capable of inhibiting the proliferation of cancer cell lines at a micromolar concentration. Six compounds are found to be potent against HGC cell lines; compound 15 is found to be active against HGC - Gastric, MCF7 - Breast Cancer and DU145 - Prostate Cancer cell lines; compound 39 is potent against MNK-74; four compounds are found to be potent against MCF-7 cell lines; three compounds are active against MDAMB-231; nine compounds are found to be potent against DU-145; three compounds are active against PC-3 cell lines. These compounds constitute a promising starting point for the development of novel and more potent anticancer agents in future.
