An Efficient Catalyst for Aldol Condensation Reactions

Hassan, Yusuf

doi:10.18596/jotcsa.293058

Cited by 2 publications

(2 citation statements)

References 14 publications

(14 reference statements)

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“…The oily crude products thus obtained were purified by column chromatography to give the required arylidenylcyclohexanone derivatives in good to moderate yields (55–68%). These molecules were characterized on the basis of their spectroscopic data and are supported by previous literature. − The appropriately substituted tetrahydroquinazolinamines 4 were accessed by condensation of respective arylidenylcyclohexanones 3 with guanidine hydrochloride in the presence of NaH in dimethylformamide (DMF) as the solvent following earlier reported protocols , (Scheme ). The reaction involves conjugate 1, 4 addition of guanidine to the olefinic bond of the enone followed by cyclization and condensation at the carbonyl end, tautomerization, and aromatization by aerial oxidation, resulting in the formation of the 2-aminopyrimidine nucleus.…”

Section: Resultsmentioning

confidence: 71%

Novel Tetrahydroquinazolinamines as Selective Histamine 3 Receptor Antagonists for the Treatment of Obesity

et al. 2019

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The histamine 3 receptor (H3R) is a presynaptic receptor, which modulates several neurotransmitters including histamine and various essential physiological processes, such as feeding, arousal, cognition, and pain. The H3R is considered as a drug target for the treatment of several central nervous system disorders. We have synthesized and identified a novel series of 4-aryl-6-methyl-5,6,7,8tetrahydroquinazolinamines that act as selective H3R antagonists. Among all the synthesized compounds, in vitro and docking studies suggested that the 4-methoxy-phenyl-substituted tetrahydroquinazolinamine compound 4c has potent and selective H3R antagonist activity (IC 50 < 0.04 μM). Compound 4c did not exhibit any activity on the hERG ion channel and pan-assay interference compounds liability. Pharmacokinetic studies showed that 4c crosses the blood brain barrier, and in vivo studies demonstrated that 4c induces anorexia and weight loss in obese, but not in lean mice. These data reveal the therapeutic potential of 4c as an anti-obesity candidate drug via antagonizing the H3R.

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Section: Resultsmentioning

confidence: 71%

Novel Tetrahydroquinazolinamines as Selective Histamine 3 Receptor Antagonists for the Treatment of Obesity

et al. 2019

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“…The synthesis of CH-5 was achieved by aldol condensation, using the general procedure reported by Hassan and co-authors, with minor modifications [ 49 ]. Briefly, 5 mL cyclohexanone (Sigma-Aldrich ® , St. Louis, MO, USA) was added to a solution of 10 mL 4-formylbenzonitrile (Sigma-Aldrich ® ) in methanol (10 mL).…”

Section: Methodsmentioning

confidence: 99%

The Curcumin Analog CH-5 Exerts Anticancer Effects in Human Osteosarcoma Cells via Modulation of Transcription Factors p53/Sp1

Lima

Seba

Silva

et al. 2018

IJMS

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Curcumin is a potential anticancer drug with poor bioavailability, which limits its clinical use as a therapeutic agent. The aim of this study was a preliminary evaluation of the curcumin analogue CH-5 as a cytotoxic agent in human osteosarcoma cell lines U2OS, MG-63, and Saos-2. CH-5 inhibited cell viability at lower concentrations than curcumin, leading to the induction of apoptosis. The cellular levels of the transcription factors p53 and Sp1 affect the expression of cellular pathways that lead to apoptosis. CH-5 increased p53 protein levels in U2OS cells and reduced Sp1 levels, with a consequent effect on the expression of their target genes DNA methyltransferase 1 (DNMT1) and growth arrest and DNA damage-inducible 45 alpha gene (Gadd45a). CH-5 repressed DNMT1 and increased Gadd45a mRNA expression, which was dependent on p53, as this effect was only observed in the colorectal cancer cell line HCT116 with active p53, but not in the isogenic p53-deficient HCT116 cells. CH-5 also reduced the protein levels of DNMT1, which led to the upregulation of Gadd45a. These results suggest that CH-5 has potentially higher anticancer activity than curcumin, which is associated with the expression of apoptosis-associated genes regulated by the transcription factors Sp1 and p53. Future work on CH-5 will define the therapeutic potential of this compound in vivo.

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An Efficient Catalyst for Aldol Condensation Reactions

Abstract: A new manganese complex was synthesised around S,S-1,2diaminocyclohexane linked ketopinic acid scaffold, and successfully utilised as a catalyst in the aldol condensation reactions of benzaldehyde with various aliphatic ketones to obtain products with excellent yield of >99%.

Cited by 2 publications

References 14 publications

Novel Tetrahydroquinazolinamines as Selective Histamine 3 Receptor Antagonists for the Treatment of Obesity

Novel Tetrahydroquinazolinamines as Selective Histamine 3 Receptor Antagonists for the Treatment of Obesity

The Curcumin Analog CH-5 Exerts Anticancer Effects in Human Osteosarcoma Cells via Modulation of Transcription Factors p53/Sp1

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