A simple and efficient three components domino reaction of γ-butyrolactam (2-pyrrolidinone), aromatic aldehyde and substituted thiophenol catalyzed by elemental iodine resulted in the formation of 1-((phenylthio)(phenyl)methyl)pyrrolidin-2-one derivatives. The stability of the synthesized analogues was evaluated in stimulated gastric fluid (SGF) and bovine serum albumin (BSA). In vitro anticancer activity was investigated in the low micromolar range and a few analogues were found to possess good activity. This current protocol provides several advantages like shorter reaction time, excellent yield and convenient work-up. © 2012 The Royal Society of Chemistry.

Sathiyanarayanan K

Department of Chemistry

School of Advanced Sciences

Vellore Campus

Gunasekar ramachandran

Ramachandran G

Natesan sundaramoorthy karthikeyan

Karthikeyan N.S

Kulathu iyer sathiyanarayanan

Periyasamy giridharan

Vellore Institute of Technology (VIT) is a private university located in&nbsp;Tamil Nadu, India. Founded in 1984, as Vellore Engineering College, the institution offers 20 undergraduate, 34 postgraduate, four integrated and four research programs. It has campuses in Vellore, Amravati, Bhopal and Chennai.

VIT is one of the top ranked private universities in India according to NIRF, THE and QS Rankings.&nbsp;Govt. of India has recognized&nbsp;VIT, Vellore as an&nbsp;Institution of Eminence. This has allowed VIT to take independent quality initiatives and move up in world ranking.

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VIT University

Organic & Biomolecular Chemistry

An efficient and modest protocol has been utilized for the synthesis of bicyclic dilactam derivatives through one-pot multicomponent domino reaction starting from various cyclic ketones under mild condition. The synthesized motif shows four stereogenic centers with two quaternary amine functionalities and such molecular arrangements are very fascinating and rare to obtain. We propose a mechanism for the formation of bicyclic dilactams through aldol condensation/condensation of cyanoacetamides/cyclization of condensed intermediate. © 2018, © 2018 Taylor &amp; Francis.

Synthetic Communications

Synthesis of highly functionalized strained bicyclic dilactam derivatives

A new sulfur-bearing phenanthridine probes were synthesized and examined for their cation recognition abilities towards different cations in aqueous ACN solution and paper strips.

New Journal of Chemistry

Development of paper-based chemosensor for the detection of mercury ions using mono- and tetra-sulfur bearing phenanthridines

A series of 1-((2-hydroxynaphthalen-1-yl)(phenyl)(methyl))pyrrolidin-2-one derivatives by an efficient iodine catalyzed domino reaction involving various aromatic aldehydes, 2-pyrrolidinone and β-naphthol was achieved and the structures were elucidated by FTIR 1H NMR, 13C NMR, and HRMS. Subsequently they were evaluated for cytotoxicity against breast cancer (MCF-7), colon cancer (HCT116) cell lines. In the cytotoxicity, the relative inhibition activity was remarkably found to be high in MCF-7 cell lines as 79% (4c), 83% (4f) and the IC50values were 1.03µM (4c), 0.98µM (4f). Compounds 4a, 4e, 4k-m, and 4q were found to be inactive and rest showed a moderate activity. In order to get more insight into the binding mode and inhibitor binding affinity, compounds (4a-q) were docked into the active site phosphoinositide 3-kinase (PI3K) (PDB ID: 4JPS) which is a crucial regulator of apoptosis or programmed cell death. Results suggested that the hydrophobic interactions in the binding pockets of PI3K exploited affinity of the most favourable binding ligands (4c and 4f: inhibitory constant (ki)=66.22nM and 107.39nM). The SAR studies demonstrated that the most potent compounds are 4c and 4f and can be developed into precise PI3K inhibitors with the capability to treat various cancers.

Bioorganic & Medicinal Chemistry Letters

Iodine catalyzed three component synthesis of 1-((2-hydroxy naphthalen-1-yl)(phenyl)(methyl))pyrrolidin-2-one derivatives: Rationale as potent PI3K inhibitors and anticancer agents

A simple and highly efficient protocol has been developed for the synthesis of triazatricyclo[6.2.2.01,6]dodecane-9,12-dione (TATCD) derivatives. Use of metal hydroxide catalyst in the presence of protic solvent plays a key role in these reaction transformations. Mechanistic studies specify that the proposed mechanism proceeds only via aldol reaction, condensation, cyclization, and dehydration to form the desired product. This current protocol provides several advantages such as use of a readily available precursor, consumption of less energy, short reaction time, moderate to good yields, and convenient workup. © 2015 Taylor and Francis Group, LLC.

Domino Reaction for the Synthesis of Highly Functionalized Triazatricyclo[6.2.2.01,6]dodecane

The diastereoselective direct one-pot three-components Mannich reaction of cyclododecanone (CDD), which has a unique conformation with aromatic aldehydes and anilines in the presence of catalytic amount of ammonium acetate was studied. The catalyzed reaction offered high yield, high diastereoselectivity, and simple workup. The addition of aniline to the aldol product took place, and this addition was made to the less hindered α-side. The Mannich derivatives were found to exhibit anti-cancer activities against six human cancer cell lines. This was observed using the CCK-8 nonradioactive colorimetric assay and the results were compared with MCFA10 normal breast epithelium cell line. A significant difference was observed in anti-cancer activity of anti (7f-7h) and syn (7ff-7hh) isomers in human cancer cell lines. Graphical abstract: The diastereoselective direct one-pot three-components, Mannich reaction of CDD, having unique conformation, with aromatic aldehydes and anilines in the presence of catalytic amount of NH4OAc giving anti/syn products was studied. The β-amino-carbonyl compounds are potent human anti-cancer cell lines and analogues of 7h-g anti-isomers are active in anti-cancer cell line whereas 7hh-gg syn-isomer is inactive.[Figure not available: see fulltext.] © 2014 Springer Science+Business Media New York.

Medicinal Chemistry Research

A mild and efficient one-pot three-component synthesis of anti-β-amino-carbonyl compounds catalyzed by NH4OAc and their anticancer activities

The title compound, C 21H 20O 2S 2, forms a propeller-shaped structure with the tetra-hedral C atom as the central hub and meth-oxy-benzene and phenyl residues as radiating blades. Short C - H⋯π contacts are observed.

Fulltext

Acta Crystallographica Section E Structure Reports Online

1-Methoxy-4-({[(4-methoxyphenyl)sulfanyl](phenyl)methyl}sulfanyl)benzene

Accounts of Chemical Research

Strategies for Innovation in Multicomponent Reaction Design

Domino Reactions in Organic Synthesis

Tetrahedron Letters

Molecular iodine-catalyzed one-pot synthesis of substituted quinolines from imines and aldehydes

Angewandte Chemie International Edition

Preview: Angew. Chem. Int. Ed. 44/2005

Efficient iodine catalyzed three components domino reaction for the synthesis of 1-((phenylthio)(phenyl)methyl)pyrrolidin-2-one derivatives possessing anticancer activities

Journal	Data powered by TypesetOrganic & Biomolecular Chemistry
Publisher	Data powered by TypesetRoyal Society of Chemistry (RSC)
ISSN	1477-0520
Open Access	0