An efficient approach to the synthesis of tri-substituted iminothiazolidenes and their effects on the human neuroblastoma cell line (original) (raw)
European Journal of Chemistry, 2018
By addition of semicarbazide or phenylhydrazine hydrochloride to thienoylisothiocyanate (1) resulted in building of thiosemicarbazide derivative (2), triazole derivative (4) and thiophene-2-carboxamide (5), respectively. Basic cyclization of compound 2 led to formation of oxadiazine (3). Synthesis of thiadiazine derivative (6) was achieved via reaction of compound 5 and maleic anhydride in triethyl amine. Heating of compound 5 with ethyl chloroacetate or sodium ethoxide produced thiadiazine derivative (7) and triazolethione (8), respectively. Thiosemicarbazide derivative 11 was synthesized by addition of nicotinic hydrazide to compound 1. Refluxing of compound 11 with lead acetate afforded triazole (13). Moreover, acid and base mediated cyclizations of compound 11 gave thiadiazole (12) and 1,2,4-triazolethione (14) throughout thiophene intermediate, respectively. Addition of ethyl 2-aminothiophene-3-carboxylate to compound 1 formed thiourea (15) which was refluxed with ethoxide givi...
European journal of medicinal chemistry, 2019
A small library of 3-(5-imidazo[2,1-b]thiazolylmethylene)-2-indolinones has been synthesized and screened according to protocols available at the National Cancer Institute (NCI). Some derivatives were potent antiproliferative agents, showing GI50 values in the nanomolar range. Remarkably, when most active compounds against leukemia cells were tested in human peripheral blood lymphocytes from healthy donors, were 100-200 times less cytotoxic. Some compounds, selected by the Biological Evaluation Committee of NCI, were examined to determine tubulin assembly inhibition. Furthermore, flow cytometric studies performed on HeLa, HT-29, and A549 cells, showed that compounds 14 and 25 caused a block in the G2/M phase. Interestingly, these derivatives induced apoptosis through the mitochondrial death pathway, causing in parallel significant activation of both caspase-3 and -9, PARP cleavage and down-regulation of the anti-apoptotic proteins Bcl-2 and Mcl-1. Finally, compound 25 was also teste...
Journal of Saudi Chemical Society, 2015
A novel series of 2-(3-(4-oxo-2-substituted phenyl thiazolidin-3-yl)phenyl)benzo[d] thiazole-6-carboxylic acid derivatives PP1-PP8 were synthesized by various benzothiazole Schiff's bases by reaction with thioglycollic acid. Their structures were established on the basis of IR, 1 H-NMR, 13 C-NMR, mass spectral data and elemental analysis. All the synthesized compounds were screened for their in vitro anticancer activity by 3-(4,5-dimethyl thiazole-2yl)-2,5diphenyltetrazoliumbromide (MTT) assay on human cervical cancer cell line (HeLa) cell lines. Among these compound PP2 exhibited most significant activity as compared with PP5, PP7 and PP8. However, the activity was less as compared to the standard drug Cisplatin.
Novel Synthesis of some thiazolidinone derivatives
Developed simple and efficient method in synthesis of some derivatives of thiazolidine by using easily available reagents. The synthesis of 5-(4-substituted benzylidene)-3-[(anilino) methyl]-1, 3-thiazolidene-2,4-dione (III a-f) has been carried out from Synthesis of thiazolidene-2, 4-dione (I) by using the reaction of chloro acetic acid and thiourea in presence of green and universal solvent i.e. water followed by reaction of (I) with substituted benzaldehyde and sodium acetate in presence of acid afforded 5-(substituted benzylidene)-1,3-thiazolidene-2,4-dione (IIa-b) which further treatment with formaldehyde in ethanol in presence of acid gave IIIa-f. The resulting products were purified by column chromatography using n-hexane and ethyl acetate as solvent system and recrystalised by water and ethanol while it has been characterized by IR, 1H NMR, Mass spectroscopic method and elemental analysis.
A new synthetic route to aminothiazolinones
2003
Novel 2 (5 R 1,3,4 thiadiazol 2 yl)aminothiazolin 4 ones 6a-h and 2 imino 3 (5 R 1,3,4 thiadiazol 2 yl)thiazolidin 4 ones 7a-h were prepared by treating N (5 R 1,3,4 thiadiazol 2 yl)thioureas 4a-h with chloroacetic acid on various solid supports under micro wave irradiation. Tautomeric mixtures of compounds 6a-h and 7a-h were obtained in all cases. In alkaline and neutral media, compounds 6a-h were the major products, while in acid media, 7a-h were the major products
Key compound 2-(4-amino-5-oxo-3-(thiophene-2-ylmethyl)-4,5-dihydro-1,2,4-tiazole-1-yl) acetohydrazide (3) was synthesized by reacting hydrazine hydrate with ethyl-2-(4-amino-5-oxo-3-(thiophene-2-ylmethyl)-4,5-dihydro-1,2,4-tiazole-1yl)acetate (2), obtained in basic media from 4-amino-5-(thiophene-2-ylmethyl)-2H-1,2,4-triazole-3(4H)-one (1). Compound 3 was converted to thiosemicarbazide derivatives (4aed) and Schiff base derivatives 6aee and 7aee. The treatment of compound 4 with NaOH gave 4-amino-2-((4-(4-aryl)-5-mercapto-4H-1,2,4-triazole-3-yl)methyl)-5-(thiophene-2-ylmethyl)-2H-1,2,4-triazole-3(4H)-ones (5aed). All newly compounds, well characterized by elemental analyses, IR, 1 H NMR, 13 C NMR and mass spectral studies were tested for their antioxidant and antimicrobial activities. Thiosemicarbazide derivatives (4aed) were highly active in two antioxidant tests with 69.0e88.2% DPPH scavenging and 503e1257 mM TEAC values, while the others showed lower or no activity. The results of the two antioxidant tests correlated well. Moreover, Thiosemicarbazide derivatives (4aed) also showed antibacterial activity against Staphylococcus aureus, Bacillus cereus, and Mycobacterium smegmatis. Thiosemicarbazide group deserves attention in the synthesis of bioactive compounds.
— Thiazolidinone belongs to important groups of heterocyclic compounds. Recently this compounds displays activities such as antioxidants, anti-inflammatory, anti-virus and tuberculostatic. In this project we reported an effective reaction to synthesis of novel thiazolidinone-4-one in the presence of deep Eutectic Solvent as catalyst by Aldol condensation, derivatives of thiourea asymmetric and aldehydes.The primary deivatives phenyl thiourea were obtained by the reaction of derivatives Aniline with Ammonium thiocyanate and HCl in refluxing free solvent and Next reaction between deivatives phenyl thiourea and chloro acetyl chloride in refluxing ethanol. Subsequent synthesis of 5-Arylidene-2-imino-4-thiazolidinones was performed by condensation of amino thiazolidinone with aldehydes in the presence of catalysts Deep Eutectic Solvent. This method have several advantage such as synthesis free solvent, short duration of action, the use of catalysts deep eutectic solvent, being environmentally friendly and simple procedure.The structure of synthesized compounds (3f-h) characterized by infra-red spectroscopy (FTIR), 1 H Nuclear magnetic resonances, and 13 C Nuclear magnetic resonances.
Synthesis of bis-thiazolidin-4-ones from N,N,N″-(1,ω-alkanediyl)bis(N″-organylthiourea) derivatives
Zeitschrift für Naturforschung B, 2015
A new series of (2Z,2′E)-dimethyl 2,2′-[(2Z,2′Z)-3,3′-(alkanediyl)bis(4-oxo-2-iminothiozolidin-3-yl-5-ylidene)]acetates has been synthesized by the reaction of N,N″-(1,ω-alkanediyl)bis(N′-organylthiourea) derivatives with dimethyl acetylenedicarboxylate. The structures were established by spectroscopic data, elemental analyses, and single crystal X-ray crystallography. A rationale for the formation of the products is presented.
European Journal of Medicinal Chemistry, 2014
Key compound 2-(4-amino-5-oxo-3-(thiophene-2-ylmethyl)-4,5-dihydro-1,2,4-tiazole-1-yl) acetohydrazide (3) was synthesized by reacting hydrazine hydrate with ethyl-2-(4amino-5-oxo-3-(thiophene-2-ylmethyl)-4,5-dihydro-1,2,4-tiazole-1yl)acetate (2), obtained in basic media from 4-amino-5-(thiophene-2-ylmethyl)-2H-1,2,4-triazole-3(4H)-one (1). Compound 3 was converted to thiosemicarbazide derivatives (4a-d) and Schiff base derivatives 6a-e and 7a-e. The treatment of compound 4 with NaOH gave 4-amino-2-((4-(4aryl)-5-mercapto-4H-1,2,4-triazole-3-yl)methyl)-5-(thiophene-2-ylmethyl)-2H-1,2,4-triazole-3(4H)-ones (5a-d). All newly compounds, well characterized by elemental analyses, IR, 1 H NMR, 13 C NMR and mass spectral studies were tested for their antioxidant and antimicrobial activities. Thiosemicarbazide derivatives (4a-d) were highly active in two antioxidant tests with 69.0-88.2% DPPH• scavenging and 503-1257 µM TEAC values, while the others showed lower or no activity. The results of the two antioxidant tests correlated well. Moreover, Thiosemicarbazide derivatives (4a-d) also showed antibacterial activity against S. aureus, B. cereus, and M. smegmatis. Thiosemicarbazide group deserves attention in the synthesis of bioactive compounds.
2022
A series of new usnic acid ketamine compounds [1-8] and their oxime analogues [9-12] were synthesized by reacting (+)-usnic acid with various amines and subsequent treatment with hydroxylamine hydrochloride. They were evaluated on the human glioblastoma-astrocytoma cell line (U87MG) by a MTT assay for cell viability in vitro. The ketamine-derivatives (Schiff bases) show significant cytotoxicity on U87MG cells. A novel N-heterocyclic derivative (1,4-diazepine) showed an interesting tautomeric structure and displayed more activity on cancer cell line than (+)-usnic acid itself.