502618-33-9

Upstream product

• 555-16-8 4-nitrobenzaldehdye 
• 530-93-8 1,2,3,4-tetrahydronaphthalen-2-one 

Downstream Products

• 909778-46-7 1-((4-nitrophenyl)(piperidin-1-yl)methyl)naphthalene-2-ol 

Relevant academic research and scientific papers

Cytotoxic 1,3-diarylidene-2-tetralones and related compounds

A number of 1,3-arylidene-2-tetralones 1, 2 and 4 were synthesised and demonstrated cytotoxic activity towards murine P388 and L1210 cells as well as human Molt 4/C8 and CEM T-lymphocytes. In general, the related 1-arylidene-2-tetralones 3 possessed lower potencies in these screens than the compounds in series 1 and 4. Approximately, half of the compounds were evaluated against a panel of human tumour cell lines. In this screen, most of the enones were more cytotoxic than the established anticancer agent melphalan and some demonstrated selective toxicity towards leukemic and colon cancer cells. The modes of action of representative compounds include interfering with the biosyntheses of nucleic acids and proteins as well as altering redox potentials. The compounds were well tolerated when administered intraperiteonally to mice. Thus these novel enones are promising prototypic molecules due to their potent cytotoxic properties and lack of significant murine toxicity.

Cytotoxic 5-aryl-1-(4-nitrophenyl)-3-oxo-1,4-pentadienes mounted on alicyclic scaffolds

The 5-aryl-1-(4-nitrophenyl)-3-oxo-1,4-pentadienyl pharmacophore was incorporated into four series of compounds 1-4. Compounds 1a-g comprised a cluster of 3-arylidene-1-(4-nitrophenylmethylene)-2-oxo-3,4-dihydro-1H-naphthalenes while the analogues 2a-g co

Experimental and theoretical investigations on acid catalysed stereoselective synthesis of new indazolyl-thiazole derivatives

1-Arylidene-2-tetralone (2), obtained from condensation of 2-tetralone and aromatic aldehydes in acetic acid and HCl, on condensation with thiosemicarbazide in acidic and alkaline medium afforded tetrahydro-2H-benzo[e]indazole-2-carbothioamide as trans (3) and cis (4) diastereoisomers of 1-H and 9b-H respectively. The synthesis of new indazolyl-thiazol-4(5H)-ones (5) from trans isomer (3) and α-halo acids is reported. A DFT study along with single crystal X-ray diffraction data of a representative compound (5a) is presented. The chemistry of the reaction of indazole-2-carbothioamides with methyl iodide, DMAD and acetic anhydride is described. Eight newly synthesised compounds were screened for their antibacterial and antifungal activities. Some of the compounds have shown promising antimicrobial activities.

Spectral, DFT and X-ray diffraction studies on regioselective synthesis of thiazolo-quinazoline system

Unsymmetrical quinazoline-3-thione 2, obtained from one pot condensation of 2-tetralone, p-chlorobenzaldehyde and thiourea in acidic medium, on reaction with α-halo acids afforded thiazolo-quinazoline derivatives 3, 7 and not their regioisomers 4 and 8 respectively. The cyclised product obtained by the reaction of thione 2 with 1,2-dibromoethane has been assigned structure 5. Condensation of thione 2 with 3-chloropropionic acid and 1,3-dibromopropane furnished thiazino-quinazoline derivatives 10 and 12 instead of their regioisomers 11 and 13 respectively. The structure of the cyclised products has been established by means of spectral data (IR, NMR and Mass). X-ray diffraction studies of a representative compound supported our claim on structural assignments. DFT studies on regioisomers further validated the claim for assigned structures. The reaction of thione 2 with 3-chloropropionc acid in presence of acetic acid yielded thiazinan-4-one 10.

Novel synthesis of 2-naphthol Mannich bases and their NMR behaviour

A novel two-step procedure involving the formation of 1-arylidene-2- tetralones from 2-tetralone and subsequent Michael addition of a cyclic secondary amine on the alkenone followed by in situ aerial oxidation was developed to produce 2-naphthol Mannich bases. A simple microwave-assisted one-pot synthesis of 2-naphthol Mannich bases was also carried out under solvent-free conditions from 2-naphthol and corresponding aldehydes and amines in the presence of p-toluenesulfonic acid. The compounds of this series displayed interesting NMR behaviour. Extensive variable-temperature NMR investigations, including HSQC experiments, are herein reported. NMR results on the conformation in solution phase were found to be consistent with the X-ray crystal structure in the solid state.