A new direct synthetic access to 4-amino-2-N-(glycosyl/propyl)-1,2,4-triazole-3-thiones via hydrazinolysis of 3-N-((acylated glycosyl)/allyl)-1,3,4-oxadiazole-2-thiones

Boraei, Ahmed T. A.

doi:10.3998/ark.5550190.p009.399

Cited by 9 publications

(8 citation statements)

References 20 publications

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“…The target chalcones were precipitated and subsequently underwent filtration and recrystallization from EtOH to give pure compounds [18]. 4-Amino-1,2,4-triazole-3-thione derivative 1 was prepared according to the procedures [22].…”

Section: Synthesis Of Chalconesmentioning

confidence: 99%

Synthesis and Anti-Proliferative Assessment of Triazolo-Thiadiazepine and Triazolo-Thiadiazine Scaffolds

et al. 2019

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A series of triazolo-thiadiazepines 4a–k were synthesized with excellent yields using dehydrated PTSA as a catalyst in toluene. Two triazolo-thiadiazines were obtained; 8a was formed directly by reflux in ethanol, whereas, PTSA promoted the formation of 8b. The molecular structure of the formed triazolo-thiadiazepines is identical to the imine-form 4a–k and not the enamine-tautomer 6a–k. The structures of the newly synthesized triazolo-thiadiazepines 4a–k and triazolo-thiadiazines 8a–b were elucidated using NMR (1H, and 13C), 2D NMR, HRMS, and X-ray single crystal. Furthermore, 4a was deduced using X-ray single crystal diffraction analysis. These new thiadiazepine hits represent an optimized series of previously synthesized indole-triazole derivatives for the inhibition of EGFR. The cytotoxicity activity against two cancer cell lines including human liver cancer (HEPG-2) and breast cancer (MCF-7) was promising, with IC50 between 12.9 to 44.6 µg/mL and 14.7 to 48.7 µg/mL for the tested cancer cell lines respectively, compared to doxorubicin (IC50 4.0 µg/mL). Docking studies revealed that the thiadiazepine scaffold presented a suitable anchor, allowing good interaction of the various binding groups with the enzyme binding regions and sub-pockets.

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Section: Synthesis Of Chalconesmentioning

confidence: 99%

Synthesis and Anti-Proliferative Assessment of Triazolo-Thiadiazepine and Triazolo-Thiadiazine Scaffolds

et al. 2019

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Section: Resultsmentioning

confidence: 99%

“…As part of our current studies on the development of new routes in heterocyclic synthesis, − here we focused on the synthesis of new heterocyclic systems from ninhydrin. Stirring ninhydrin 1 with ethyl acetoacetate 2 in water for 15 min afforded ethyl indeno[1,2- b ]furan-3-carboxylate 3 in excellent yield . Reaction of 3 with hydrazine hydrate in water or ethanol and reflux for 10 min, interestingly, afforded tetraazafluoranthen-3(2 H )-one 6 in good yield.…”

Section: Resultsmentioning

confidence: 99%

Expeditious Green Synthesis of Novel 4-Methyl-1,2,5,6-tetraazafluoranthen-3(2H)-one Analogue from Ninhydrin: N/S-Alkylation and Aza-Michael Addition

et al. 2020

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A straightforward green synthesis of 4-methyl-1,2,5,6-tetraazafluoranthen-3(2H)-one 6 is reported from ninhydrin 1 via condensation with ethyl acetoacetate, followed by cyclization with hydrazine hydrate in water as a benign solvent. Tetraazafluoranthen-3-thione 7 was obtained using Lawesson's reagent. N-alkylated tetraazafluoranthen-3-one 8−12 and Salkylated analogues 13−15 were synthesized via alkylation. The investigation of the unique reactivity of 4-methyl-1,2,5,6-tetraazafluoranthen-3(2H)-one/ thione toward the alkylation and aza-Michael additions was explored.

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“…4-Amino-5-(1H-indol-2-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thione 1 Synthetic procedures followed [33].…”

Section: Methodsmentioning

confidence: 99%

Synthesis and X-ray Crystal Structure Analysis of Substituted 1,2,4-Triazolo [4’,3’:2,3]pyridazino[4,5-b]indole and Its Precursor

et al. 2023

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The hit compound 1,2,4-triazolo[4’,3’:2,3]pyridazino[4,5-b]indole 3 was synthesized from the reflux of 4-amino-5-indolyl-1,2,4-triazole-3-thione 1 with 4′-bromoacetophenone 2 in methanol catalyzed by concentrated HCl and the desired final molecule was obtained by recrystallization from methanol. The suggested structures of compounds 1 and 3 based on the spectral characterizations were confirmed by X-ray single crystal diffraction analysis. Compound 3 crystallized in the triclinic crystal system and P-1 space group with a = 5.9308(2) Å, b = 10.9695(3) Å, c = 14.7966(4) Å, α = 100.5010(10)°, β = 98.6180(10)°, and γ = 103.8180(10)°. On the other hand, the crystal system of 1 is monoclinic, where a = 6.23510(10) Å, b = 26.0156(4) Å, c = 12.4864(2) Å, β = 93.243(2)° and the space group is P21. The triazole and indole rings are found twisted from each other in both compounds. The twist angle is higher in 3 (12.65°) than 1 (4.94–7.22°). In the case of the former, the H…H (39.6%), H…C (22.0%), N…H (12.8%) and Br…H (13.2%) contacts are the most dominant while the C…C, C…H, Br…H, N…H and S…S contacts have the characteristics of strong interactions. In the latter, the C…H, N…H, S…H, S…S, and C…C contacts are the most important. In this case, the percentages of the H…H, C…H, N…H and S…H contacts are in the range of 34.9–37.4, 20.5–24.0, 12.2–13.6, 14.0–15.8, respectively. In both systems, the shape index and curvedness of surfaces confirmed the presence of π–π stacking interactions.

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A new direct synthetic access to 4-amino-2-N-(glycosyl/propyl)-1,2,4-triazole-3-thiones via hydrazinolysis of 3-N-((acylated glycosyl)/allyl)-1,3,4-oxadiazole-2-thiones

Cited by 9 publications

References 20 publications

Synthesis and Anti-Proliferative Assessment of Triazolo-Thiadiazepine and Triazolo-Thiadiazine Scaffolds

Synthesis and Anti-Proliferative Assessment of Triazolo-Thiadiazepine and Triazolo-Thiadiazine Scaffolds

Expeditious Green Synthesis of Novel 4-Methyl-1,2,5,6-tetraazafluoranthen-3(2H)-one Analogue from Ninhydrin: N/S-Alkylation and Aza-Michael Addition

Synthesis and X-ray Crystal Structure Analysis of Substituted 1,2,4-Triazolo [4’,3’:2,3]pyridazino[4,5-b]indole and Its Precursor

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