Reaction of N,N-disubstituted hydrazinecarbothioamides with 2-bromo-2-substituted acetophenones

Aly, Ashraf A.; Hassan, Alaa A.; AbdAl-Latif, El Shimaa S. M.; Bräse, S.; Nieger, Martin

doi:10.24820/ark.5550190.p010.385

Cited by 6 publications

(9 citation statements)

References 25 publications

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“…The chemical structures of all newly synthesized compounds were confirmed based on their spectral analyses; FT-IR, 1 H, 13 C NMR, Mass Spectra as well as their elemental analysis data (see Experimental Part). with bis(methylthio)methylenemalononitrile 8 in refluxing ethanol and in the presence of TEA as catalyst gave the unexpected N,N'-diphenyl-1,3,4-thiadiazole-2,5-diamine (9) [35], instead of the expected product of 5-amino-4-cyano-3-(methylthio)-N-phenyl-1H-pyrazole-1-carbothioamide (10). The IR spectrum of 4-thiazolidinone 13 showed the disappearance of characteristic absorption bands for N-H groups, while it showed the appearance of new characteristic absorption bands at 1695 and 1717 cm -1 for carbonyl groups in both thiazolidine ring and ester group, respectively.…”

Section: Resultsmentioning

confidence: 99%

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2022

Sohag J. Sci

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In this work we studied the reaction of carbohydrazides with some reagents having electrophilic centers such as arylmethylenemalononitrile, aromatic aldehydes, bis(methylthio)methylenemalononitrile, dimethyl acetylene-dicarboxylate and cyanoguanidine. The resulting products are five-membered heterocyclic rings such as thiadiazoles, thiazoles, triazoles; and six-membered heterocyclic rings such as triazines.

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Section: Resultsmentioning

confidence: 99%

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2022

Sohag J. Sci

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“…Treatment of the 2,5‐dithiobiurea derivative 2 with an equimolar ratio of 2‐bromoacetophenone 121 in ethanol in the presence of triethyl amine at room temperature resulted in the formation of the (thiazol‐2‐ylidene)hydrazine‐1‐carbothioamide derivative 122 . However, reaction of the 2,5‐dithiobiurea derivative 2 (R═4‐tolyl) with 2‐bromoacetophenone 121 (R═Me) (1:1 ratio) under reflux afforded the bis‐(thiazol‐2‐ylidene)hydrazine derivative 123 in 74% yield (Scheme ) .…”

Section: Reactions Of Bis‐thioureasmentioning

confidence: 99%

Bis‐thiourea Derivatives and Their Utility in Synthesis of Mono‐heterocyclic, Bis‐heterocyclic, and Fused Heterocyclic Systems

Dawood

2019

Journal of Heterocyclic Chem

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Bis‐thiourea derivatives have distinguished synthetic potentialities. They are interesting substrates for construction of various classes of heterocycles, such as thiazoles, thiadiazoles, imidazoles, bis‐thiazoles, bis‐thiadiazoles, and fused heterocyclic systems. The current review is concerned on disclosing the synthetic and research applications of bis‐thioureas that were reported in the literature during the last decade.

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“…Recently, we have an interest in the preparation of heterocycles of similar structural features [15][16][17][18][19][20][21][22][23]. In addition, we prepared metal complexes of thiosemicarbazones with Cu(I) and Cu(II) and the tridentate and bidentate structures of the paracyclophanyl-thiosemicarbazone-metal complexes were elucidated [24].…”

Section: Introductionmentioning

confidence: 99%

“…Figure19. The 2D and 3D diagrams illustrate the binding mode of 3d interacting with the colchicine binding site of β-tubulin.…”

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New Paracyclophanylthiazoles with Anti-Leukemia Activity: Design, Synthesis, Molecular Docking, and Mechanistic Studies

et al. 2020

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A new series of methyl 2-(2-(4′-[2.2]paracyclophanyl)-hydrazinylidene)-3-substituted-4-oxothiazolidin-5-ylidene)acetates 3a–f were synthesized from the reaction of paracyclophanyl-acylthiosemicarbazides 2a–f with dimethyl acetylenedicarboxylate. Based upon nuclear magnetic resonance (NMR), infrared (IR), and mass spectra (HRMS), the structure of the obtained products was elucidated. X-ray structure analysis was also used as unambiguous tool to elucidate the structure of the products. The target compounds 3a–f were screened against 60 cancer cell lines. They displayed anticancer activity against a leukemia subpanel, namely, RPMI-8226 and SR cell lines. The activity of compound 3a was found as the most cytotoxic potency against 60 cancer cell lines. Consequently, it was selected for further five doses analysis according to National Cancer Institute (NCI) protocol. The cytotoxic effect showed selectivity ratios ranging between 0.63 and 1.28 and between 0.58 and 5.89 at the GI50 and total growth inhibition (TGI) levels, respectively. Accordingly, compound 3a underwent further mechanistic study against the most sensitive leukemia RPMI-8226 and SR cell lines. It showed antiproliferation with IC50 = 1.61 ± 0.04 and 1.11 ± 0.03 µM against RPMI-8226 and SR cell lines, respectively. It also revealed a remarkable tubulin inhibitory activity, compared to colchicine with IC50 = 4.97 µM/mL. Caspase-3, BAX, and Bcl-2 assays for 3a using annexin V-FITC staining revealed significant pro-apoptotic activity. Furthermore, multidrug-resistant leukemia SR cells were used to show better resistance indices (1.285 ng/mL, 1.15-fold) than the reference. Docking studies with β-tubulin indicate that most of the tested compounds illustrated good binding at the colchicine binding site of the enzyme, especially for compound 3a, which made several interactions better than that of the reference colchicine.

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Reaction of N,N-disubstituted hydrazinecarbothioamides with 2-bromo-2-substituted acetophenones

Cited by 6 publications

References 25 publications

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Bis‐thiourea Derivatives and Their Utility in Synthesis of Mono‐heterocyclic, Bis‐heterocyclic, and Fused Heterocyclic Systems

New Paracyclophanylthiazoles with Anti-Leukemia Activity: Design, Synthesis, Molecular Docking, and Mechanistic Studies

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