899-98-9Relevant academic research and scientific papers
Synthesis, molecular modeling and bio-evaluation of cycloalkyl fused 2-aminopyrimidines as antitubercular and antidiabetic agents
Singh, Nimisha,Pandey, Sarvesh Kumar,Anand, Namrata,Dwivedi, Richa,Singh, Shyam,Sinha, Sudhir Kumar,Chaturvedi, Vinita,Jaiswal, Natasa,Srivastava, Arvind Kumar,Shah, Priyanka,Siddiqui, M. Imran,Tripathi, Rama Pati
scheme or table, p. 4404 - 4408 (2011/09/12)
An economical and efficient one step synthesis of a series of 8-(arylidene)-4-(aryl)-5,6,7,8-tetrahydro-quinazolin-2-ylamines and 9-(arylidene)-4-(aryl)-6,7,8,9-tetrahydro-5H-cycloheptapyrimidin-2-ylamines by the reaction of bis-benzylidene cycloalkanones and guanidine hydrochloride in presence of NaH has been developed. All the synthesized compounds were evaluated against Mycobacterium tuberculosis H37Rv strain and the α-glucosidase and glycogen phosphorylase enzymes. Few of the compounds have shown interesting in vitro activity with MIC up to 3.12 μg/mL against M. tuberculosis and very good inhibition of α-glucosidase and glycogen phosphorylase enzymes. The most potent non toxic compound 40 exhibited about 58% ex vivo activity at MIC of 3.12 μg/mL. The present study opens a new gate to synthesize antitubercular agents for diabetic TB patients. In silico docking studies indicate that mycobacterial dihydrofolate reductase is the possible target of these compounds.
Claisen-schmidt condensation catalyzed by metal-organic frameworks
Dhakshinamoorthy, Amarajothi,Alvaro, Mercedes,Garcia, Hermenegildo
experimental part, p. 711 - 717 (2010/06/13)
Metal-organic framework [Fe(BTC) (BTC = 1,3,5-benzenetricarboxylic acid)] is a convenient heterogeneous catalyst for the carbon-carbon bond forming reaction in toluene between acetophenone and benzaldehyde to give selectively chalcone in high yield. Fe(BTC) appears as a general catalyst able to synthesize selectively different chalcone derivatives bearing various functionalities. Fe(BTC) could be recycled with no significant loss of catalytic efficiency and crystallinity in subsequent runs.
Simple access to α, β unsaturated ketones by acid-catalyzed solvent- free reactions
Le Gall, Erwan,Texier-Boullet, Fran?oise,Hamelin, Jack
, p. 3651 - 3657 (2007/10/03)
Various chalcones and dibenzylidene cycloalkanones were readily prepared in a few minutes with good yields by simply mixing aromatic aldehydes with substituted acetophenones or benzaldehyde with cycloalkanones in the presence of catalytic amounts of p-toluene sulfonic acid under focused microwave irradiation.
The synthesis and chlorosulfonation of some diarylidene and heteroarylidene ketones with varying alicyclic ring size
Cremlyn, Richard J.,Frearson, Martin J.,Graham, Stephen
, p. 205 - 218 (2007/10/03)
A series of diarylidene and heteroarylidene ketones (1-20) was prepared using alicyclic ketones ((CH2)nC=O where n=3 to 7).An improved synthesis of 2,4-dibenzylidenecyclobutanone (1) is described and the ease of preparation of the arylidene derivatives is considered in terms of the size of the alicyclic ring.Treatment of 2,5-dibenzylidenecyclopentanone (2) with chlorosulfonic acid (10 mole equivalents) afforded the 4,4'-bis-sulfonyl chloride (23), reducing the amount of chlorosulfonis acid (6 mole equivalents) produced the corresponding mono-sulfonyl chloride (24).Only the respective 4,4'-bis-sulfonyl chlorides (39, 45, 51) could be isolated from the diarylidene ketones derived from larger alicyclic rings.Attempted chlorosulfonation of 2,4-dibenzylidene cyclobutanone (1) gave a mixture of products which could not be clearly characterised.The sulfonyl chlorides were converted into stable sulfonamides (25-29, 35, 36, 38, 40-44, 46-48, 52, 54) by condensation with amines, and selected samples were screened for biological activity as potential insecticides, herbicides, and fungicides.The orientation of sulfonation is discussed in relation to stereoelectronic factors and the relevant spectral data.Key words: Arylidene and heteroarylidene ketones, chlorosulfonation, sulfonamides
Synthesis and cytotoxic evaluation of some cyclic arylidene ketones and related oximes, oxime esters, and analogs
Dimmock,Sidhu,Chen,Li,Quail,Allen,Kao
, p. 852 - 858 (2007/10/02)
A number of arylidene derivatives of alicyclic ketones and some corresponding oximes, oxime esters, and related compounds were prepared as candidate cytotoxic agents. All of the compounds were evaluated against murine L1210 lymphoid leukemia cells. In general, cytotoxicity was greatest with the α,β-unsaturated ketones and diminished with the oximes, and the oxime esters had little or no activity in this screen. When the same compounds were examined in both the in vitro L1210 and P388 leukemia screens, in the majority of cases the L1210 cells were more sensitive to these derivatives. Over half of the compounds prepared were evaluated against approximately 55 human tumors in vitro and showed selective toxicity toward one or more groups of neoplastic diseases, particularly leukemia. Some correlations between structure and bioactivity were discerned. The cytotoxicity screening and stability studies of representative compounds suggested that the ketones, oximes, and oxime esters were stable under the conditions of bioevaluation. X-ray crystallography of four representative compounds revealed structural features associated with cytotoxicity which may be considered in the design of future candidate cytotoxins.
New Aziridines and Pyrazolines Derived from Diarylidenecycloalkanones
Kabli, R. A.,Kaddah, A. M.,Khalil, A. M.,Khalaf, A. A.
, p. 152 - 156 (2007/10/02)
A number of diarylidenecycloalkanones (I and II) have been prepared by the condensation of cycloalkanones with different aromatic aldehydes.Treatment of I and II with bromine gives the corresponding tetrabromides (III and IV).Compounds III react with meth
