112854-82-7Relevant articles and documents
Phenothiazine and amide-ornamented novel nitrogen heterocyclic hybrids: synthesis, biological and molecular docking studies
Iniyaval, Shunmugam,Karuppasamy, Ayyanar,Lim, Wei-Meng,Mai, Chun-Wai,Padmavathy, Krishnaraj,Ramalingan, Chennan,Sivaramakarthikeyan, Ramar
, p. 4049 - 4060 (2020/03/19)
The synthesis of novel hybrids, namely, phenothiazine and amide-ornamented nitrogen heterocycles (25-34) has been accomplished utilizing a multi-step synthetic protocol and the structures have been established based on physical and spectral techniques. Of these, the hybrids possessing meta-nitro (26), para-fluoro (28), meta- and para-methyl (31), ortho-bromo (33) and ortho- and para-dimethyl (34) phenyl carboxamide scaffolds exhibited superior anti-inflammatory profiles over the standard diclofenac sodium. A hybrid integrated with a para-fluorophenyl carboxamide moiety (28) showed the highest DPPH radical scavenging activity among the chemical entities synthesized. Furthermore, the results of anticancer evaluations implied that the hybrid tethered with a phenyl carboxamide structural unit (29) exerted superior activity when compared with other hybrids against the pancreatic cancer cells SW1990 and AsPC1. Molecular docking between the hybrid 29 and B-cell lymphoma 2 reflects its appreciable binding affinity (-8.84 kcal mol-1). The results revealed that these chemical entities can serve as potent biological agents and/or efficient intermediates for the construction of potent biological agents.
Long-wavelength-absorbing and -emitting carbostyrils with high fluorescence quantum yields
Uray, Georg,Niederreiter, Karlheinz S.,Belaj, Ferdinand,Fabian, Walter M. F.
, p. 1408 - 1417 (2007/10/03)
Synthesis, absorption and fluorescence spectra, as well as quantum yields of a series of donor-acceptor-substituted carbostyrils (= quinolin- 2(1H)-ones), are reported. Unprecedented strong absorption maxima (ε = 10000-20000) close to the visible spectrum, large Stokes shifts up to 130 nm, and quantum yields up to 0.7 are obtained with derivatives containing donor substituents at C(6) and C(7), and either one Ph substituent at C(3) or one CF3 residue at C(4). For analytical applications in biochemistry and medicine, N(1)-functionalization, or amidoacylation at C(3) in the case of the CF3 derivatives, is possible without a concomitant hypsochromic shift of their absorption and emission maxima. Semiempirical molecular-orbital calculations (AM1 for structures, ZINDO for electronic transition energies) prove to be a suitable tool for the prediction of absorption properties of these compounds. The crystal-structure analysis of 6,7-dimethoxy-1-methyl-3- nitro-4-(trifluoromethyl)quinolin-2-(1H)-one (7) (C13H11F3N2O5, monoclinic, P2(l)lc, a=12.372(2), b= 12.154(2), c= 10.119(2)A, β= 112.95(2)°) shows that the NO2 group, squeezed between the CF?3 and the C=O group, is oriented almost perpendicularly (87.8(4)°) to the ring plane. The intramolecular F ··· N distance between the CF3 and the NO2 group is only 2.513(4)A.