30510-67-9Relevant articles and documents
Simple and Efficient Amberlite 15-catalyzed Synthesis of Dihydroquinazolinones
Krishnaji, T.,Murthy, V. N.,Raghunadh, A.,Rao, L. V.
, p. 1468 - 1475 (2020)
Abstract: The Amberlite 15 catalyzed synthesis of substituted 2,3-dihydroquinazolin-4(1H)-ones was reported. The reaction conditions were optimized by screening in different solvents and catalysts. The substrate scope of the reaction was also studied, and
Efficient synthesis of 6,6a-dihydroisoindolo[2,1-a]quinazoline-5,11-dione derivatives catalyzed by functionalized nanoporous silica
Rayatzadeh, Ayeh,Haghipour, Sirous
, p. 103 - 107 (2021/02/05)
An efficient and facile method has been developed for the synthesis of various 6,6a-dihydroisoindolo[2,1-a]quinazoline-5,11-dione derivatives, via a three-component reaction of 2-amino-N-(R)-benzamide derivatives with 2-formylbenzoic acid using sulfonic acid functionalized nanoporous silica as an efficient catalyst in ethanol under reflux. High yield of the desired products, reusability of the catalyst, and effortless workup step without using chromatography are the advantages of this method. Graphic abstract: [Figure not available: see fulltext.]
Design, synthesis, in vitro and in silico biological assays of new quinazolinone-2-thio-metronidazole derivatives
Ansari, Samira,Asgari, Mohammad Sadegh,Biglar, Mahmood,Esfahani, Ensieh Nasli,Hamedifar, Haleh,Larijani, Bagher,Mahdavi, Mohammad,Mohammadi-Khanaposhtani, Maryam,Rastegar, Hossein,Tas, Recep,Taslimi, Parham
, (2021/07/08)
A new series of quinazolinone-2-thio-metronidazole derivatives 9a-o was designed, synthesized and assayed for their activities against metabolic enzymes human carbonic anhydrase I and II (hCAs I and II), acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and α-glucosidase. The results indicated that all the synthesized compounds exhibited excellent inhibitory activities against mentioned enzymes as compared with standard inhibitors. Representatively, the most potent compound against CA enzymes, 4-fluorophenyl derivative 9i, was 4 and 7-times more potent than standard inhibitor acetazolamide against hCA I and II, respectively; 4-fluorobenzyl derivative 9m as the most potent compound against cholinesterase enzymes, was around 11 and 21-times more potent than standard inhibitor tacrine against AChE and BChE, respectively; the most active α-glucosidase inhibitor 9h with 4-methoxyphenyl moiety was 5-times more active that acarbose as standard inhibitor. Furthermore, in order to study interaction modes of the most potent compounds in the active site of their related enzymes, molecular modeling was performed. Druglikeness, ADME, and toxicity profile of the compounds 9i, 9m, and 9h were also predicted.
Design and synthesis of diphenylpyrimidine derivatives (DPPYs) as potential dual EGFR T790M and FAK inhibitors against a diverse range of cancer cell lines
Ai, Min,Wang, Changyuan,Tang, Zeyao,Liu, Kexin,Sun, Xiuli,Ma, Tengyue,Li, Yanxia,Ma, Xiaodong,Li, Lei,Chen, Lixue
, (2019/11/26)
A new class of pyrimidine derivatives were designed and synthesized as potential dual FAK and EGFRT790M inhibitors using a fragment-based drug design strategy. This effort led to the identification of the two most active inhibitors, namely 9a and 9f, against both FAK (IC50 = 1.03 and 3.05 nM, respectively) and EGFRT790M (IC50 = 3.89 and 7.13 nM, respectively) kinase activity. Moreover, most of these compounds also exhibited strong antiproliferative activity against the three evaluated FAK-overexpressing pancreatic cancer (PC) cells (AsPC-1, BxPC-3, Panc-1) and two drug-resistant cancer cell lines (breast cancer MCF-7/adr cells and lung cancer H1975 cells) at concentrations lower than 6.936 μM. In addition, 9a was also effective in the in vivo assessment conducted in a FAK-driven human AsPC-1 cell xenograft mouse model. Overall, this study offers a new insight into the treatment of hard to treat cancers.
Synthesis and biological evaluation of quinoline-quinazolinones for antimicrobial and antileishmanial potential
Tiwari, Shweta,Kirar, Seema,Banerjee, Uttam Chand,Babu, Neerupudi Kishore,Singh, Sushma,Singh, Inder Pal
, p. 1251 - 1258 (2020/12/04)
In an attempt to find a new class of antimicrobial and antileishmanial agents, a series of twenty-three quinoline-quinazolinones were prepared via reaction of 8-hydroxy/methoxyquinoline-2-carbaldehyde with various substituted aminobenzamides. These compounds were screened for their antimicrobial activity against Gram-positive bacteria (B. subtilis), Gram-negative bacteria (E. coli and P. putida) and fungus (C. viswanathii) and antileishmanial activity against promastigotes of L. donovani. Compound 28k exhibited highest activity against B. subtilis with an IC50 of 0.17±0.07 M while compound 28j exhibited highest activity against promastigotes of L. donovani with an IC50 of 6±0.0 M.
A novel approach for the synthesis of functionalized hydroxylamino derivative of dihydroquinazolinones
Jaganmohan, Chikkanti,Vinay Kumar,Venkateshwarlu,Mohanty, Sandeep,Kumar, Jaydeep,Venkateswara Rao,Raghunadh, Akula,Tadiparthi, Krishnaji
supporting information, p. 2163 - 2170 (2020/06/10)
A new metal-free and modular approach for the synthesis of various functionalized dihydroquinazolinones has been developed from isatoic anhydride, amines, 4-chloro-N-hydroxybenzimidoylchloride to yield up to 71%. The reaction has been screened in various bases, solvents at different temperatures. The substrate scope of the reaction has been studied with various amines and the possible reaction mechanism for this reaction has also been proposed.
Novel quinazolin–sulfonamid derivatives: synthesis, characterization, biological evaluation, and molecular docking studies
Sepehri, Nima,Mohammadi-Khanaposhtani, Maryam,Asemanipoor, Nafise,Hosseini, Samanesadat,Biglar, Mahmood,Larijani, Bagher,Mahdavi, Mohammad,Hamedifar, Haleh,Taslimi, Parham,Sadeghian, Nastaran,Norizadehtazehkand, Mostafa,Gulcin, Ilhami
, (2020/11/27)
In the design of novel drugs, the formation of hybrid molecules via the combination of several pharmacophores can give rise to compounds with interesting biochemical profiles. A series of novel quinazolin–sulfonamid derivatives (9a–m) were synthesized, characterized and evaluated for their in vitro antidiabetic, anticholinergics, and antiepileptic activity. These synthesized novel quinazolin–sulfonamid derivatives (9a–m) were found to be effective inhibitor molecules for the α-glycosidase, human carbonic anhydrase I and II (hCA I and hCA II), butyrylcholinesterase (BChE) and acetylcholinesterase (AChE) enzyme, with Ki values in the range of 100.62 ± 13.68–327.94 ± 58.21 nM for α-glycosidase, 1.03 ± 0.11–14.87 ± 2.63 nM for hCA I, 1.83 ± 0.24–15.86 ± 2.57 nM for hCA II, 30.12 ± 3.81–102.16 ± 13.87 nM for BChE, and 26.16 ± 3.63–88.52 ± 20.11 nM for AChE, respectively. In the last step, molecular docking calculations were made to compare biological activities of molecules against enzymes which are achethylcholinesterase, butyrylcholinesterase and α-glycosidase. Communicated by Ramaswamy H. Sarma.
Palladium-Catalyzed Oxidative Three-Component Coupling of Anthranilamides with Isocyanides and Arylboronic Acids: Access to 2,3-Disubstituted Quinazolinones
Qian, Chun,Liu, Kui,Tao, Shou-Wei,Zhang, Fang-Ling,Zhu, Yong-Ming,Yang, Shi-Lin
, p. 9201 - 9209 (2018/07/13)
A novel palladium-catalyzed oxidative three-component coupling of easily accessible N-substituted anthranilamides with isocyanides and arylboronic acids is achieved. This protocol offers an alternative approach toward 2,3-disubstituted quinazolinones with a wide substrate scope and good functional group tolerance.
De novo synthesis of 2,2-bis(dimethylamino)-3-alkyl or benzyl 2,3-dihydroquinazolin-4(1H)-one compounds
Jaganmohan, Chikkanti,Vinay Kumar,Sandeep Reddy,Mohanty, Sandeep,Kumar, Jaydeep,Venkateswara, Rao,Tadiparthi, Krishnaji,Raghunadh, Akula
supporting information, p. 168 - 174 (2018/01/01)
A new versatile and efficient strategy for the synthesis of 2,2-bis(dimethylamino)-3-alkyl or benzyl 2,3-dihydroquinazoline-4(1H)-one compounds has been developed by one-pot multicomponent reaction with isatoic anhydride, amines followed by in situ-generated Vilsmeier reagent. The reaction has also been studied with different amines and solvents.
Ionic liquid supported on magnetic nanoparticles as a novel reusable nanocatalyst for the efficient synthesis of tetracyclic quinazoline compounds
Ghorbani-Choghamarani, Arash,Taherinia, Zahra,Nikoorazm, Mohsen
, p. 6591 - 6604 (2018/07/03)
A magnetic ionic liquid supported on γ-Fe2O3 nanocatalyst was synthesized successfully and characterized by Fourier transform infrared spectroscopy, vibrating sample magnetometry, thermogravimetric analysis, differential scanning calorimetry, X-ray diffraction and scanning electron microscopy. The resulting nano-Fe3O4-supported, ionic liquid was an efficient catalyst for preparation of a series of tetracyclic quinazoline compounds by three components reaction of a mixture of isatoic anhydride and amine with ninhydrin in PEG and the desired products were obtained in good to excellent yields. High efficiency, waste-free, mild reaction conditions, effortless magnetic recovery and reusability up to four continuous cycles are the noteworthy features of the currently employed heterogeneous catalytic system.
