28565-98-2Relevant academic research and scientific papers
O-amino aromatic amide derivative as well as preparation method and application thereof
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, (2021/08/14)
The invention discloses an o-amino aromatic amide derivative as well as a preparation method and application thereof. The o-amino aromatic amide derivative is a compound with a structural general formula I, II and III or a pharmaceutically acceptable salt
Antitumor, cytotoxic, and antioxidant evaluation of six heterocyclic compounds containing different heterocycle moieties
Abdallah, Suzan Abdelhalim,El-Hashash, Maher Abdel-Aziz,Radwan, Tasneem Mokhtar,Wasfy, Ashraf Abdel-Hamid Farouk
, (2020/02/04)
Heterocyclic compounds with different heterocycle moieties, namely benzoxazinone, benzimidazole, quinazolinone, and benzofuranone heterocyclic rings, were synthesized, characterized, and evaluated for their anticancer activity against human hepatocellular carcinoma cell line (HepG2) using sulforhodamine B (SRB) and dimethylthiazol-diphenyltetrazolium bromide (MTT) assays. Also, their cytotoxic activities were tested against human epithelioid carcinoma (Hela) cell line in comparison with normal cell, amniotic epithelial (WISH) cell line, as an in vitro toxicity estimation model. The results showed clearly that 2-(2-benzyl-4-oxoquinazolin-3(4H)-yl)acetohydrazide 4 is the most potent antioxidant and anticancer agents. Although, 3-amino-2-benzylquinazolin-4(3H)-one 5 is less potent anticancer agent against Hela but it is more safe against normal cell (WISH).
Design, synthesis and biological activity of selective hCAs inhibitors based on 2-(benzylsulfinyl)benzoic acid scaffold
Rotondi, Giulia,Guglielmi, Paolo,Carradori, Simone,Secci, Daniela,De Monte, Celeste,De Filippis, Barbara,Maccallini, Cristina,Amoroso, Rosa,Cirilli, Roberto,Akdemir, Atilla,Angeli, Andrea,Supuran, Claudiu T.
, p. 1400 - 1413 (2019/08/26)
A large library of derivatives based on the scaffold of 2-(benzylsulfinyl)benzoic acid were synthesised and tested as atypical inhibitors against four different isoforms of human carbonic anhydrase (hCA I, II, IX and XII, EC 4.2.1.1). The exploration of the chemical space around the main functional groups led to the discovery of selective hCA IX inhibitors in the micromolar/nanomolar range, thus establishing robust structure-activity relationships within this versatile scaffold. HPLC separation of some selected chiral compounds and biological evaluation of the corresponding enantiomers was performed along with molecular modelling studies on the most active derivatives.
Enantioselective Synthesis of 3-Arylquinazolin-4(3H)-ones via Peptide-Catalyzed Atroposelective Bromination
Diener, Matthew E.,Metrano, Anthony J.,Kusano, Shuhei,Miller, Scott J.
supporting information, p. 12369 - 12377 (2015/10/12)
We report the development of a tertiary amine-containing β-turn peptide that catalyzes the atroposelective bromination of pharmaceutically relevant 3-arylquinazolin-4(3H)-ones (quinazolinones) with high levels of enantioinduction over a broad substrate scope. The structure of the free catalyst and the peptide-substrate complex were explored using X-ray crystallography and 2D-NOESY experiments. Quinazolinone rotational barriers about the chiral anilide axis were also studied using density functional theory calculations and are discussed in light of the high enantioselectivities observed. Mechanistic studies also suggest that the initial bromination event is stereodetermining, and the major monobromide intermediate is an atropisomerically stable, mono-ortho-substituted isomer. The observation of stereoisomerically stable monobromides stimulated the conversion of the tribromide products to other atropisomerically defined products of interest. For example, (1) a dehalogenation Suzuki-Miyaura cross-coupling sequence delivers ortho-arylated derivatives, and (2) a regioselective Buchwald-Hartwig amination procedure installs para-amine functionality. Stereochemical information was retained during these subsequent transformations.
Synthesis of some new glutamine linked 2,3-disubstituted quinazolinone derivatives as potent antimicrobial and antioxidant agents
Prashanth,Revanasiddappa
, p. 2665 - 2676 (2013/07/26)
A series of novel glutamine linked 2,3-disubstituted quinazolinone conjugates was synthesized from methyl anthranilate and different substituted acids and acid chlorides. The compounds 5a-l were prepared in good yields. All compounds were screened for their antibacterial activity against Gram-positive and Gram-negative bacteria and for antifungal activity against Candida albicans and Aspergillus flavus using paper disk diffusion technique. The minimum inhibitory concentrations of the compounds were also determined by agar streak dilution method. The compound 5b was found to exhibit the most potent in vitro anti-microbial activity. When tested for their antioxidant activity, compounds 5i and 5l showed potent radical scavenging activity, while compound 5g had moderate effect against 2,2-diphenyl-1-picrylhydrazyl, hydroxyl, nitric oxide, and superoxide radical scavenging assays. These results suggest that, the three quinazolinone analogs (5g, 5i, and 5l) could be considered as useful templates for future development to obtain more potent antioxidant agents.
Synthesis of poly(pyridazinoquinazolones)
Ponomarev,Razorenov,Petrovskii
, p. 2376 - 2384 (2014/05/06)
A model reaction of 2-alkyl-3-aminoquinazolones with α-dicarbonyl compounds benzil and its 4,4′-derivatives, acenaphthenequinone and isatin was studied for the first time. The reaction proceeded in pentafluorophenol and led to the formation of new heterocyclic systems. This approach was used in the synthesis of new thermostable polyheteroarylenes with fluorescent properties, viz., poly(pyridazinoquinazolones).
Nonpeptide inhibitors of measles virus entry
Sun, Aiming,Prussia, Andrew,Zhan, Weiqiang,Murray, Ernest E.,Doyle, Joshua,Cheng, Li-Ting,Yoon, Jeong-Joong,Radchenko, Eugene V.,Palyulin, Vladimir A.,Compans, Richard W.,Liotta, Dennis C.,Plemper, Richard K.,Snyder, James P.
, p. 5080 - 5092 (2007/10/03)
Measles virus (MV) is one of the most infectious pathogens known. Despite the existence of a vaccine, over 500 000 deaths/year result from MV or associated complications. Anti-measles compounds could conceivably reverse these statistics. Previously, we described a homology model of the MV fusion protein trimer and a putative binding site near the head-neck region. The resulting model permitted the identification of two nonpeptidic entry inhibitors. Here, we present the design, synthesis, and bioevaluation of several series of fusion inhibitors and describe their structure-activity relationships (SAR). Five simply substituted anilides show low-μM blockade of the MV, one of which (AS-48) exhibits IC50 = 0.6-3.0 μM across a panel of wild-type MV strains found in the field. Molecular field topology analysis (MFTA), a 2D QSAR approach based on local molecular properties (atomic charges, hydrogen-bonding capacity and local lipophilicity), applied to the anilide series suggests structural modifications to improve potency.
A new synthesis of 2-substituted 4H-3,1-benzoxazin-4-ones by cyanuric chloride cyclodehydration of N-benzoyl- and N-acylanthranilic acids
Khajavi, Mohammad S.,Shariat, Seyed M.
, p. 1159 - 1165 (2007/10/03)
A new and a convenient method for the synthesis of aryl- and alkyl-2-substituted 4H-3,1-benzoxazin-4-ones by cyclodehydration of N-benzoyl- and N-acylanthranilic acid by cyanuric chloride is described.
Green chemical multi-component one-pot synthesis of fluorinated 2,3-disubstituted quinazolin-4(3H)-ones under solvent-free conditions and their anti-fungal activity
Dandia, Anshu,Singh, Ruby,Sarawgi, Pritima
, p. 1835 - 1840 (2007/10/03)
A rapid one-pot solvent-free procedure has been developed for the synthesis of fluorinated 2,3-disubstituted quinazolin-4(3H)-ones by neat three-component cyclocondensation of anthranilic acid, phenyl acetyl chloride and substituted anilines under microwa
