16313-65-8Relevant articles and documents
Synthesis, crystal structure, spectroscopic and photophysical studies of novel fluorinated quinazoline derivatives
Kushwaha, Narva Deshwar,Zamisa, Sizwe J.,Kushwaha, Babita,Sharma, Anamika,Kayamba, Francis,Merugu, Srinivas Reddy,Ganai, Ab Majeed,Obakachi, Vincent A.,Albericio, Fernando,Karpoormath, Rajshekhar
, (2021)
A novel small library of seven fluorinated quinazoline derivatives was synthesized and for four of them, the crystal structures were solved by single X-ray diffractometer and compared the confirmation of molecules in solution-phase using 2D NOESY experiments. Taking advantage of the series prepared, we were able to describe the influence of various substituents on the core scaffold (fluorinated quinazoline) on its molecular conformations’ intermolecular interactions and on the photoluminescent properties. The Hirshfeld surfaces were used to investigate the structure-directing effects of functional groups in controlling their solid-state behavior. Theoretical DFT calculations were carried out for getting additional knowledge on crystal-state interactions as compared to a gas phase. The photo-physical (UV and fluorescence) properties of all compounds have been studied. among the series, five compounds exhibited excellent photoluminescent properties.
A solvent- And catalyst-free tandem reaction: Synthesis, and photophysical and biological applications of isoindoloquinazolinones
Ali, Sk Asraf,Bera, Anirban,Ikbal, Mohammed,Manna, Susanta Kumar,Misra, Sandip,Saha, Amit,Samanta, Shubhankar
supporting information, p. 4324 - 4331 (2020/03/26)
An easy green synthetic approach for fused isoindoloquinazolinones has been developed under neat reaction (yields up to 91%) conditions. This new one-pot tandem methodology involves condensation of readily available anthranilamide with 3-(2-formylcycloalk
Fluorescent biaryl uracils with C5-dihydro- And quinazolinone heterocyclic appendages in PNA
Heidari, Ali,Ghorbani-Choghamarani, Arash,Hajjami, Maryam,Hudson, Robert H.E.
, (2020/04/29)
There has been much effort to exploit fluorescence techniques in the detection of nucleic acids. Canonical nucleic acids are essentially nonfluorescent; however, the modification of the nucleobase has proved to be a fruitful way to engender fluorescence. Much of the chemistry used to prepare modified nucleobases relies on expensive transition metal catalysts. In this work, we describe the synthesis of biaryl quinazolinone-uracil nucleobase analogs prepared by the condensation of anthranilamide derivatives and 5-formyluracil using inexpensive copper salts. A selection of modified nucleobases were prepared, and the effect of methoxy- or nitro- group substitution on the photophysical properties was examined. Both the dihydroquinazolinone and quinazolinone modified uracils have much larger molar absorptivity (~4-8×) than natural uracil and produce modest blue fluorescence. The quinazolinone-modified uracils display higher quantum yields than the corresponding dihydroquinazolinones and also show temperature and viscosity dependent emission consistent with molecular rotor behavior. Peptide nucleic acid (PNA) monomers possessing quinazolinone modified uracils were prepared and incorporated into oligomers. In the sequence context examined, the nitro-substituted, methoxy-substituted and unmodified quinazolinone inserts resulted in a stabilization (?Tm = +4.0/insert; +2.0/insert; +1.0/insert, respectively) relative to control PNA sequence upon hybridization to complementary DNA. All three derivatives responded to hybridization by the “turn-on” of fluorescence intensity by ca. 3-to-4 fold and may find use as probes for complementary DNA sequences.
