Synthesis, Crystal Structure and Antiproliferative Activity of 6-Adamantyl-3-aryl[1,2,4]triazolo[3,4-b][1,3,4]thiadiazoles

Abstract

A series of 3,6-disubstituted [1,2,4]triazolo [3,4-b][1,3,4]thiadiazoles 5a -l bearing an adamantyl moiety were synthesized by condensation of 4-amino-5-aryl-2H-1,2,4-triazole-3(4H)-thiones 4a -l with adamantyl-1-carboxylic acid in the presence of POCl 3 . The structures of the newly synthesized compounds were established using spectroanalytical techniques and verified further by the crystal structure determination of compounds 5a and 5j. The compounds were screened for their antiproliferative activity against a large panel of human cell lines.

Synthesis, anti-HIV activity and molecular modeling study of 3-aryl-6-adamantylmethyl-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole derivatives

“…In continuation of our study on the discovery of potent HIV-1 non-nucleoside reverse transcriptase inhibitors [24][25][26][27][28] aiming to produce new generation inhibitors that circumvent the viral resistance, we designed a new series of 3-aryl-6-adamantylmethyl- [1,2,4]triazolo [3,4-b] [1,3,4]thiadiazoles 6a-l, in addition to studying their molecular docking with the HIV reverse transcriptase amino acids. In addition, the antifungal and antibacterial activities were screened.…”

Structural and Energetic Properties of Weak Noncovalent Interactions in Two Closely Related 3,6-Disubstituted-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole Derivatives: In Vitro Cyclooxygenase Activity, Crystallography, and Computational Investigations

“…Furthermore, the CSD search detected 51 hits containing different substituents attached to atom C9 of the triazole ring and atom C7 of the thiadiazole ring. Five of these compounds have an adamantane cage attached to a thiadiazole ring (CSD refcodes: BOTYEP, UPAVIR, VUNLUM, VUNMAT, and WADHIU). − Unlike compound 1 , which has an adamantane cage attached to a triazole ring, we identified eight structures containing monosubstituted (CSD refcodes: NITSIV, ILETOK, LEPQED, QEMMUR, and SAPRAD, UXIPOI), ,− disubstituted (CSD refcode: XOYWOZ), and trisubstituted (csd refocde: GAJCUS) halophenyl groups. The halogen atoms are either Cl or F or both present at different positions of the phenyl ring.…”

Nascent pharmacological advancement in adamantane derivatives

“…[130] Remdesivir was taken as the reference drug. In the first and second experiments, amantadine (75) displayed a concentration-dependent reduction of viral nucleic acids 26 h and 72 h after infection, respectively. Tanner et al have synthesized a class of adamantane-based bananin derivatives and examined them for their in vitro inhibitory potential against SARS coronavirus (SCV) helicase.…”

“…Khan et al [75] 31 97.6% inhibition of proliferation MEM enhanced the activity. Rodríguez et al [76] Abbreviation: SAR, structure-activity relationship.…”