2293-07-4Relevant articles and documents
Thiazolidine-4-one clubbed pyrazoles hybrids: Potent α-amylase and α-glucosidase inhibitors with NLO properties
Duhan, Meenakshi,Kadyan, Kulbir,Kumar, Parvin,Panihar, Neeraj,Saini, Sangeeta,Sindhu, Jayant
, p. 1573 - 1587 (2020)
Molecular hybrids based on thiazolidin-4-one and pyrazolyl pharmacophore (THZP) as new antidiabetic agents were synthesized. Two sets of signals came into view in 1H NMR of THZP8-THZP14 exhibited the presence of a configurational isomeric mixture of 2E,5Z (38.24%-41.58%) and 2Z,5Z isomers (58.42%-61.76%), which was further endorsed by density functional theory (DFT) studies. All the compounds exhibit promising nonlinear optical properties (NLO). Further, the biological potential of THZPs was explored in terms of α-amylase and α-glucosidase inhibition. DFT-based descriptors were calculated to describe the reactivity, and a relationship was developed with biological activities. THZP9 and THZP14 showed remarkable inhibition of α-amylase and α-glucosidase with IC50 9.90μM and 4.84μM, respectively, as compared with standard drug acarbose.
Discovery of aminothiazole derivatives as novel human enterovirus A71 capsid protein inhibitors
Cai, Yang,Chen, Yinuo,Dong, Chune,Lan, Ke,Lei, Ping,Tang, Qi,Wu, Shuwen,Xu, Ting,Xu, Zhichao,Zhou, Hai-Bing,Zou, Wenting
, (2022/03/15)
Enterovirus A71 (EV-A71), one of the major pathogens that causes hand, foot and mouth disease (HFMD), has seriously threatened the health and safety of young children. In this study, aminothiazole derivatives were synthesized and screened against EV-A71 in Rhabdomyosarcoma (RD) cells. The best compound (12s), with a biphenyl group, showed activity against EV-A71 (EC50: 0.27 μM) but also against a series of different human enteroviruses without significant cytotoxicity (CC50 > 56.2 μM). Mechanistic studies including time-of-drug-addition assays, viral entry assays and microscale thermophoresis (MST) experiments, showed that 12s binds to EV-A71 capsid and blocks the binding between the viral protein VP1 and the relevant human scavenger receptor class B member 2 (hSCARB2).
Convenient Multicomponent One-Pot Synthesis of 2-Iminothiazolines and 2-Aminothiazoles Using Elemental Sulfur Under Aqueous Conditions
ábrányi-Balogh, Péter,Domján, Attila,Gao, Qinghe,Han, Xinya,Keser?, Gy?rgy M.,Marlok, Bence,Németh, András Gy.
supporting information, p. 3587 - 3597 (2021/07/22)
Herein, we present a novel one-pot aqueous reaction for the synthesis of 2-iminothiazolines and 2-aminothiazoles using isocyanides, amines, sulfur, and 2′-bromoacetophenones. The three-component preparation of thioureas is followed by the one-pot cyclization leading to the heterocyclic product. This efficient and mild procedure features excellent step- and atom-economy and enables the chromatography-free preparation of diversely substituted 2-iminothiazoline and 2-aminothiazole derivatives.
Green and efficient synthesis of thioureas, ureas, primary: O -thiocarbamates, and carbamates in deep eutectic solvent/catalyst systems using thiourea and urea
Bagherzadeh, Nastaran,Sardarian, Ali Reza,Inaloo, Iman Dindarloo
supporting information, p. 11852 - 11858 (2021/07/12)
An efficient and general catalysis process was developed for the direct preparation of various primary O-thiocarbamates/carbamates as well as monosubstituted thioureas/ureas by using thiourea/urea as biocompatible thiocarbonyl (carbonyl) sources. This procedure used choline chloride/tin(ii) chloride [ChCl][SnCl2]2 with a dual role as a green catalyst and reaction medium to afford the desired products in moderate to excellent yields. Moreover, the DES can be easily recovered and reused for seven cycles with no significant loss in its activity. Besides, the method shows very good performance for synthesizing the desired products on a large scale.
Eco-efficient one-pot tandem synthesis of 1-aryl-1H-tetrazol-5-amine by CAN via in situ generated 1-phenylthiourea and heterocumulene
Kondhare, Dasharath D.,Bhadke, Venkat V.,Deshmukh, Sushma S.,Wakhradkar, Mahesh G.,Totawar, Balaji B.
, (2021/07/28)
A simple, cost-effective, environmentally benign, and efficient one-pot tandem approach to the synthesis of pharmaceutically important 1-aryl-1H-tetrazole-5-amines 3a-k and 4a-k has been described. The reaction utilized 1-phenyl thiourea, which was generated in situ from aqueous ammonia and isocyanates 1a-k, for the formation of heterocumenes using sodium azide, triethylamine, and ceric ammonium nitrate (CAN) to obtain various aryl-substituted 1H-tetrazole-5-amines (3a-k) in good to excellent yields.
Design, synthesis, and antipoliferative activities of novel substituted imidazole-thione linked benzotriazole derivatives
El-Malah, Afaf,Khayyat, Ahdab N.,Malebari, Azizah M.,Mohamed, Khaled O.
, (2021/10/12)
A new series of benzotriazole moiety bearing substituted imidazol-2-thiones at N1 has been designed, synthesized and evaluated for in vitro anticancer activity against the different cancer cell lines MCF-7(breast cancer), HL-60 (Human promyelocytic leukemia), and HCT-116 (colon cancer). Most of the benzotriazole analogues exhibited promising antiproliferative activity against tested cancer cell lines. Among all the synthesized compounds, BI9 showed potent activity against the cancer cell lines such as MCF-7, HL-60 and HCT-116 with IC50 3.57, 0.40 and 2.63 μM, respectively. Compound BI9 was taken up for elaborate biological studies and the HL-60 cells in the cell cycle were arrested in G2/M phase. Compound BI9 showed remarkable inhibition of tubulin polymerization with the colchicine binding site of tubulin. In addition, compound BI9 promoted apoptosis by regulating the expression of pro-apoptotic protein BAX and anti-apoptotic proteins Bcl-2. These results provide guidance for further rational development of potent tubulin polymerization inhibitors for the treatment of cancer.
Design, synthesis and biological evaluation of novel N,4-diphenylthiazol-2-amine derivatives
Nadaf, AfraQuasar A.,Barretto, Delicia A.,Najare, Mahesh S.,Mantur, Shivaraj,Garbhagudi, Manjunatha,Gaonkar, Supreet,Joshi, Shrinivas,Khazi, Imtiyaz Ahmed M.
, p. 442 - 458 (2020/01/03)
Novel N,4-diphenylthiazol-2-amine derivatives were designed and synthesized employing Hantzsch method. The three-step reaction involved in the synthesis occurred at a faster rate with excellent yields in eco-friendly conditions. The synthesized derivatives were characterized by spectral techniques such as 1H NMR, 13C NMR, FT-IR and GCMS. Single-crystal X-ray diffraction studies also confirmed the formation of title compounds. These compounds were evaluated in vitro for their antimicrobial and anti-inflammatory activities. The results demonstrated that most of the tested compounds showed potent antifungal activity. Interestingly, these compounds also exhibited good anti-inflammatory and moderate antibacterial activity towards sensitive as well as resistant bacterial strains. In silico studies depicted their good binding affinity profile against S. aureus (PDB ID: 1AD4) and C. albicans (PDB ID: 1AI9). [Figure not available: see fulltext.].
Identification of: N -benzothiazolyl-2-benzenesulfonamides as novel ABCA1 expression upregulators
Cao, Feng,Gao, Xinfeng,Jiang, Xinhai,Li, Wenyan,Liu, Hongtao,Tian, Wenhua,Wang, Ruizhi,Wei, Liping,Xu, Chen,Xu, Yanni
, p. 411 - 418 (2020/04/15)
ATP binding cassette transporter A1 (ABCA1) is a critical transporter that mediates cellular cholesterol efflux from macrophages to apolipoprotein A-I (ApoA-I). Therefore, increasing the expression level of ABCA1 is anti-atherogenic and ABCA1 expression upregulators have become novel choices for atherosclerosis treatment. In this study, a series of N-benzothiazolyl-2-benzenesulfonamides, based on the structure of WY06 discovered in our laboratory, were designed and synthesized as novel ABCA1 expression upregulators. Based on an in vitro ABCA1 upregulatory cell model, ABCA1 upregulation of target compounds was evaluated. Compounds 6c, 6d, and 6i have good upregulated ABCA1 expression activities, with EC50 values of 0.97, 0.37, and 0.41 ΜM, respectively. A preliminary structure-activity relationship is summarized. Replacing the methoxy group on the benzothiazole moiety of WY06 with a fluorine or chlorine atom and exchanging the ester group with a cyano group resulted in more potent ABCA1 upregulating activity. Moreover, compound 6i increased ABCA1 mRNA and protein expression and significantly promoted cholesterol efflux in RAW264.7 cells. In conclusion, N-benzothiazolyl-2-benzenesulfonamides were identified as novel ABCA1 expression upregulators.
Design, synthesis and antimicrobial study of novel 1-(1,3-benzothiazol-2-yl)-3-chloro-4H-spiro[azetidine-2,3'-indole]-2',4(1'H)-diones through ketene–imine cycloaddition reaction
Agarwal, Dinesh Kr.,Agarwal, Shikha,Gandhi, Divyani,Prajapat, Prakash,Sethiya, Ayushi
, p. 141 - 148 (2020/02/04)
The present study deals with the synthesis of novel 1-(1,3-benzothiazol-2-yl)-3-chloro-4H-spiro[azetidine-2,3'-indole]-2',4(1'H)-dione derivatives from the reaction of 3-(1,3-benzothiazol-2-ylimino)-1,3-dihydro-2H-indol-2-one derivatives with chloroacetyl chloride in the presence of triethyl-amine (TEA). The mechanism involved simple acid or base catalysed reaction through the formation of Schiff base followed by cyclisation via ketene–imine cycloaddition reaction. All synthesized compounds were characterized by FT-IR,1H-NMR,13C-NMR, and elemental analysis. The antimicrobial activities of the synthesized derivatives 5a-5g were examined via Micro Broth Dilution method against bacterial strains Bacillius subtilis, Staphylcoccus aureus, E. coli, P. aeruginosa, and fungal strain Candida albicans for determining MIC values. Ampicillin, chloramphenicol, and griseofulvin were used as standard drugs. The MIC values for antimicrobial activity of synthesized compounds were examined using Micro Broth Dilution method. Compounds 5a, 5b, and 5c were found effective against E. coli (MTCC 442) and P.aeruginosa (MTCC 441) and all compounds showed moderate to excellent activity against Streptococcus aureus (MTCC 96) and Bacillius subtilis (MTCC 441). Regarding the antifungal screening, compounds 5a, 5b, and 5c exhibited excellent activity against Candida albicans MTCC 227. 1-(1,3-benzothiazol-2-yl)-3-chloro-4H-spiro[azetidine-2,3'-indole]-2',4(1'H)-dione derivatives may be used as potential lead molecules as effective antimicrobial agents.
Synthetic (E)-3-phenyl-5-(phenylamino)-2-styryl-1,3,4-thiadiazol-3-ium chloride derivatives as promising chemotherapy agents on cell lines infected with HTLV-1
Chaves, Otávio Augusto,De Oliveira, Thais Silva,Echevarria, Aurea,Echevarria-Lima, Juliana,Netto-Ferreira, José C.,Paiva, Rojane O.,Sousa-Pereira, Danilo
, (2020/06/29)
Synthesis of four compounds belonging to mesoionic class, (E)-3-phenyl-5-(phenylamino)-2-styryl-1,3,4-thiadiazol-3-ium chloride derivatives (5a-d) and their biological evaluation against MT2 and C92 cell lines infected with human T-cell lymphotropic virus type-1 (HTLV-1), which causes adult T-cell leukemia/lymphoma (ATLL), and non-infected cell lines (Jurkat) are reported. The compounds were obtained by convergent synthesis under microwave irradiation and the cytotoxicity was evaluated using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assays. Results showed IC50 values of all compounds in the range of 1.51-7.70 μM in HTLV-1-infected and non-infected cells. Furthermore, it was observed that 5b could induce necrosis after 24 h for Jurkat and MT2 cell lines. The experimental (fluorimetric method) and theoretical (molecular docking) results suggested that the mechanism of action for 5b could be related to its capacity to intercalate into DNA. Moreover, the preliminary pharmacokinetic profile of the studied compounds (5a-d) was obtained through human serum albumin (HSA) binding affinity using multiple spectroscopic techniques (circular dichroism, steady-state and time-resolved fluorescence), zeta potential and molecular docking calculations. The interaction HSA:5a-d is spontaneous and moderate (Ka ～ 104 M-1) via a ground-state association, without significantly perturbing both the secondary and surface structures of the albumin in the subdomain IIA (site I), indicating feasible biodistribution in the human bloodstream.
