《One-pot multicomponent synthesis of novel 3, 4-dihydro-3-methyl-2(1H)-quinazolinone derivatives and their biological evaluation as potential antioxidants, enzyme inhibitors, antimicrobials, cytotoxic and anti-inflammatory agents》 was written by Farooq, Samra; Mazhar, Aqsa; Ihsan-Ul-Haq; Ullah, Naseem. Electric Literature of C5H12N2 And the article was included in Arabian Journal of Chemistry in 2020. The article conveys some information:
A series of 3,4-dihydro-3-methyl-2(1H)-quinazolinones I [R = pyrrolidin-1-yl, 1-piperidyl, morpholino, etc.] with amines and formaldehyde were designed and synthesized by a reflux condensation reaction in the presence of an acid catalyst resulted in N-Mannich bases. Mannich bases I were evaluated pharmacol. for their antioxidant, α-amylase enzyme inhibition, antimicrobial, cell cytotoxicity and anti-inflammatory activities. Most of the compounds I exhibited potent activities against these bioassays. Among them, compounds I [R = 1-piperidyl, N-acetyl-4-hydroxyanilino] showed potent antioxidant activity against DPPH free radical at IC50 of 9.94 ± 0.16μg/mL and 11.68 ± 0.32μg/mL, resp. Compounds I [R = N-phenylanilino, N-acetylanilino, N-acetyl-4-hydroxyanilino] showed significant resulted in TAC and TRP antioxidant assays, comparable to that of ascorbic acid. Compounds I [R = morpholino, pyrrolidin-1-yl] showed potent activity in inhibiting α-amylase enzyme at IC50 of 10.17 ± 0.23μg/mL and 9.48 ± 0.17μg/mL, resp., when compared with acarbose (13.52 ± 0.19μg/mL). Compound I [R = N-phenylanilino] was the most active against Gram-pos. and Gram-neg. bacterial strains, compound I [R = N-acetyl-4-hydroxyanilino] was the most potent against P. aeruginosa inhibited its growth up to 80% (MIC = 11.11μg/mL). Compounds I [R = dipropylamino, 4-methylpiperazin-1-yl, piperazin-1-yl] exhibited significant activity against some fungal strains. Among the thirteen N-Mannich bases I, four were screened out based on the results of brine shrimp lethality assay (LD50) and cell cytotoxicity assay (IC50),determine their anti-cancer potential against Hep-G2 cells. The study was conducted for 24, 48, and 72 h. Compound I [R = diethylamino] showed potent results at IC50 of 6.48μM at 72 h when compared with cisplatin (2.56μM). An in-vitro nitric oxide (NO) assay was performed to shortlist compounds for in-vivo anti-inflammatory assay. Among shortlisted compounds, I [R = N-acetyl-4-hydroxyanilino] exhibited potent anti-inflammatory activity by decreasing the paw thickness to the maximum compared to the standard, acetylsalicylic acid (ASA). The experimental process involved the reaction of 1-Methylpiperazine(cas: 109-01-3Electric Literature of C5H12N2)
1-Methylpiperazine(cas: 109-01-3) can be used as mimic template in the preparation of molecularly imprinted microspheres (MIMs). It was also used to prepare the difunctional strong anion-exchange stationary phase from a 1,4-diazacyclohexane derivative..Electric Literature of C5H12N2
Referemce:
Piperazine – Wikipedia,
Piperazines – an overview | ScienceDirect Topics