Ecofriendly and highly efficient microwave-induced synthesis of novel quinazolinone-undecyl hybrids with in vitro antitumor activity

New 1,3,4-thiadiazoles as potential anticancer agents: pro-apoptotic, cell cycle arrest, molecular modelling, and ADMET profile

“…As a part of our ongoing research that aims at developing simple and efficient synthetic techniques for the synthesis of novel heterocyclic compounds with potential anticancer applications, [21][22][23][24][25][26][27][28][29][30][31] the present study reported the synthesis of numerous new substituted 1,3,4-thiadiazole derivatives incorporating benzene moiety. N-(5-Amino-1,3,4-thiadiazol-2-yl) benzamide (2) was synthesized as a sole product through reaction of benzoylisothiocyanate with thiosemicarbzide in dry acetonitrile and then underwent cyclization according to the previously published methodology [32][33][34][35][36] (Scheme 1).…”

Phthalic anhydride (PA): a valuable substrate in organic transformations

“…The adduct was tested in vitro against a panel of three human tumor cell lines, namely, Hepatocellular Carcinoma (liver) HepG2, colon cancer HCT-116, and mammary gland breast MCF-7, which demonstrated satisfactory activity (Scheme 43). 154 Zare's group in 2019 performed the reaction PA (1) and phenyl hydrazine (49) in (A): microdroplets (the reaction condition: N 2 atmosphere, DMF was demonstrated to be the best solvent for this microdroplet reaction, with a yield of product (122) up to 98% when the distance between the spray tip to the glass vial extended to 7 cm with reaction time of about 350 ms), and (B): bulk-phase without catalyst and without reuxing (the concentration of the both substrates is 10 mM). The microdroplet reaction led to signicant formation of (122) with a small amount of product (123), whereas the bulk-phase reaction of PA and (49) in acetic acid catalyst under hightemperature reuxing led to product (122), but without catalyst at room temperature only (123) was formed.…”

“…The adduct was tested in vitro against a panel of three human tumor cell lines, namely, Hepatocellular Carcinoma (liver) HepG2 , colon cancer HCT-116 , and mammary gland breast MCF-7 , which demonstrated satisfactory activity ( Scheme 43 ). 154 …”

“…Martin and Seoane in 1992 claimed that 2-thenoylbenzoic acid (146), obtained from PA (1) and 2-thenoylmagnesium iodide (154), yielded thieno[2,3-b]-l,4-naphthoquinone (147) (Scheme 54). 166 Fieser and Hershbe in 1937 reported the reaction of PA and a-tetralylmagnesium bromide (155) yielded the 2-(a-tetraloy1)benzoic acid (156) as colorless prisms, which was reduced to 2-((5,6,7,8-tetrahydronaphthalen-1-yl)methyl)benzoic acid (157) by high pressure hydrogenation (Scheme 55).…”

Synthesis and antimicrobial study of new tetrazole, benzimidazole and N3-functionalized quinazolinone derivatives

“…iQuinazolinone skeleton iis ifrequently iencountered ias ia ibuilding iblock ifor ihundreds iof inaturally ioccurring ialkaloids i [1,2]. i iSynthesis iof iquinazolinone iheterocycles ihas ibroad iimportance iin iorganic isynthesis iaccording ito itheir iextensive iimportance iin imedicinal ichemistry ibecause iof itheir idiverse ipharmacological iactivities iincluding iantibacterial i [3,4,46], iantimalarial i [5], iantifungal i [6][7][8]47], i iantihypertensive i [9,10], iantihistaminic i [11], ia ilocal ianesthetic i[12], ianti-iParkinson i [13], icardiotonic i [14], ianticancer i [15][16][17][18][19][20][21], iantiviral i [22,23] iand ithymidylate isynthase iinhibitory iactivities i [24]. iSeveral isimple iand icondensed iquinazolines iare ialso iknown ito iexhibit ipotent iCNS iactivities ias ian ianalgesic i [25], ianti-inflammatory i [26][27][28] iand ianticonvulsant iactivities i [29,30].…”