34637-85-9Relevant academic research and scientific papers
Regioselective Synthesis of 2° Amides Using Visible-Light-Induced Photoredox-Catalyzed Nonaqueous Oxidative C-N Cleavage of N, N-Dibenzylanilines
Neerathilingam, Nalladhambi,Bhargava Reddy, Mandapati,Anandhan, Ramasamy
supporting information, p. 15117 - 15127 (2021/10/25)
A visible-light-driven photoredox-catalyzed nonaqueous oxidative C-N cleavage of N,N-dibenzylanilines to 2° amides is reported. Further, we have applied this protocol on 2-(dibenzylamino)benzamide to afford quinazolinones with (NH4)2S2O8 as an additive. Mechanistic studies imply that the reaction might undergo in situ generation of α-amino radical to imine by C-N bond cleavage followed by the addition of superoxide ion to form amides.
A magnetically retrievable copper ionic liquid nanocatalyst for cyclooxidative synthesis of 2-phenylquinazolin-4(3: H)-ones
Gupta, Radhika,Arora, Gunjan,Yadav, Priya,Dixit, Ranjana,Srivastava, Anju,Sharma, Rakesh Kumar
, p. 890 - 898 (2021/02/03)
In the present work, we report the design and fabrication of a copper-containing ionic liquid supported magnetic nanocatalyst via a convenient and straightforward synthetic approach for the formation of 2-phenylquinazolin-4(3H)-ones using o-aminobenzamide and benzaldehydes as the reaction partners. The successful formation and properties of the as-prepared catalyst have been thoroughly investigated using diverse physico-chemical techniques including FT-IR, XRD, FE-SEM, TEM, ICP, VSM, BET and TGA. Using this nanocatalytic system, a variety of 2-phenylquinazolin-4(3H)-ones are synthesized in excellent yields with operational ease and short reaction times in an environmentally preferable solvent under open air and without using any external oxidizing agent. Besides, the catalyst possessed facile magnetic recoverability and remarkable reusability for six consecutive runs without any appreciable decrease in the catalytic efficiency.
Antioxidant and ros inhibitory activities of heterocyclic 2-aryl-4(3h)-quinazolinone derivatives
Choudhary, Muhammad Iqbal,Khan, Khalid Mohammed,Perveen, Shahida,Saad, Syed Muhammad
, p. 806 - 815 (2021/11/17)
Background: Antioxidants are small molecules that prevent or delay the process of oxidations caused by highly reactive free radicals. These molecules are known for their ability to protect various cellular architecture and other biomolecules from oxidative stress and free radicals. Thus, antioxidants play a key role in the prevention of oxidative damages caused by highly reactive free radicals. Methods: In the present study, a series of previously synthesized heterocyclic 2-aryl-4(3H)-quinazolinone derivatives 1-25 were screened for antioxidant activity by employing in vitro DPPH and superoxide anion radical scavenging activities. ROS inhibitory activities were also evaluated by serum-opsonized zymosan activated whole blood phagocytes and isolated neutrophils. Cytotoxicity studies were carried out by employing an MTT assay against the 3T3 cell line. Results: Most of the 2-aryl-4(3H)-quinazolinone derivatives showed potent antioxidant activities in superoxide anion radical scavenging assay with IC50 value ranging between 0.57 μM-48.93 μM, as compared to positive control quercetin dihydrate (IC50 = 94.1 ± 1.1 μM ). Compounds 5, 6, and 14 showed excellent activity in DPPH assay. Compounds 5-8, 12-15, 17, and 20 showed promising activities in the ROS inhibition assay. All compounds were found to be non-cytotoxic against the 3T3 cell line. Structure antioxidant activity has been established. Conclusion: It can be concluded that most of the heterocyclic 2-aryl-4(3H)-quinazolinone derivatives 1-25 are identified as promising antioxidant agents that are capable of fighting against free radicals and oxidative stress. Thus, they can serve as a lead towards treating oxidative stress and related pathologies.
Br?nsted acid catalyzed synthesis of 2‐aryl‐quinazolinones via cyclization of 2‐aminobenzamide with benzonitriles in PEG
Botsa, Sathish Mohan,Karasala, Bharat Kumar,Matcha, Sowbhagya Lakshmi,Vidavalur, Siddaiah
, (2021/06/14)
A simple and efficient Br?nsted acid catalyzed synthesis of 2‐aryl‐quinazolinones via cyclization of 2‐aminobenzamides with benzonitrile in PEG under metal and ligand‐free condition. All substituted benzonitriles were also well participated with the formation of the corresponding products in moderate to good yields.
Copper mediated one-pot synthesis of quinazolinones and exploration of piperazine linked quinazoline derivatives as anti-mycobacterial agents
Ahmad, Md. Naiyaz,Chopra, Sidharth,Dasgupta, Arunava,Gatadi, Srikanth,Gour, Jitendra,Kaul, Grace,Madhavi, Y. V.,Malasala, Satyaveni,Nanduri, Srinivas,Shukla, Manjulika
, p. 43533 - 43538 (2020/12/25)
A facile method was developed for the synthesis of quinazolinone derivatives in a one-pot condensation reaction via in situ amine generation using ammonia as the amine source and with the formation of four new C-N bonds in good to excellent yields. With the optimised method, we synthesized a library of piperazine linked quinazoline derivatives and the synthesized compounds were evaluated for their inhibitory activity against Mycobacterium tuberculosis. The compounds 8b, 8e, 8f, 8m, 8n and 8v showed potent anti-mycobacterial activity with MIC values of 2-16 μg mL-1. All the synthesized compounds follow Lipinski's rules for drug likeness. This journal is
Synthesis of quinazolin-4(3H)-ones via the reaction of isatoic anhydride with benzyl azides in the presence of potassium tert-butoxide in DMSO
Sayahi, Mohammad Hosein,Bahadorikhalili, Saeed,Mahdavi, Mohammad,Baghshirin, Laleh
, p. 964 - 967 (2019/11/16)
[Figure not available: see fulltext.] In this paper, a novel method is described for the synthesis of quinazolin-4(3H)-one derivatives via the reaction of isatoic anhydride with benzyl azides in the presence of potassium tert-butoxide in DMSO. The reactio
Mo (CO)6-assisted Pd-supported magnetic graphene oxide-catalyzed carbonylation-cyclization as an efficient way for the synthesis of 4(3H)-quinazolinones
Bahadorikhalili, Saeed,Ansari, Samira,Hamedifar, Haleh,Ma'mani, Leila,Babaei, Mohsen,Eqra, Rahim,Mahdavi, Mohammad
, (2019/02/14)
In this paper, a novel catalyst is introduced based on the immobilization of palladium on modified magnetic graphene oxide nanoparticles. The catalyst is characterized by several methods, including transmission electron microscopy, scanning electron microscopy, X-ray fluorescence, vibrating-sample magnetometer, Fourier transform-infrared and dynamic light scattering (DLS) analysis. The activity of the catalyst was investigated in the synthesis of 4(3H)-quinazolinones via Pd-catalyzed carbonylation-cyclization of N-(2-bromoaryl) benzimidamides by Mo (CO)6. The Mo (CO)6 is used as a carbon monoxide source for performing the reaction under mild conditions. The catalyst showed good reusability, and no change in activity was observed after 10?cycles of recovery.
Copper (II)-supported polyethylenimine-functionalized magnetic graphene oxide as a catalyst for the green synthesis of 2-arylquinazolin-4(3H)-ones
Sayahi, Mohammad Hosein,Bahadorikhalili, Saeed,Saghanezhad, Seyyed Jafar,Mahdavi, Mohammad
, p. 5241 - 5253 (2018/04/10)
A novel copper (II) catalyst supported on polyethylenimine-functionalized magnetic graphene oxide (denoted Cu@PEI-MGO) has been developed and applied for the cyclization of benzylacetamide with 2-aminobenzamide to afford 2-arylquinazolin-4(3H)-ones in acetonitrile as an inexpensive, non-toxic and reusable solvent medium. Cu@PEI-MGO was characterized by transmission electron microscopy, scanning electron microscopy, thermo-gravimetric analysis, and Fourier-transform infra-red spectroscopy.
Synthesis and biological investigation of 2,4-substituted quinazolines as highly potent inhibitors of breast cancer resistance protein (ABCG2)
Krapf, Michael K.,Gallus, Jennifer,Wiese, Michael
, p. 587 - 611 (2017/08/26)
Expression of ABCG2, a member of the ABC transporter superfamily, has been correlated to the clinical outcome of multiple cancers and is often associated with the occurrence of multidrug resistance (MDR) in chemotherapy. Inhibition of the transport protein by potent and selective inhibitors might be a way to treat cancer more efficiently and improve the therapy of cancer patients. Recently we reported the synthesis of new inhibitors based on a quinazoline scaffold. In the present study more structural variations were explored. Compounds with 3,4-dimethoxy groups and meta or para nitro substituents were found to be highly potent inhibitors of ABCG2. The most potent compound was more than five-fold more potent than Ko143, one of the best inhibitors of ABCG2. To determine the new compounds selectivity toward ABCG2 their inhibitory effects on ABCB1 and ABCC1 were also investigated identifying selective as well as broadspectrum inhibitors. Furthermore, intrinsic cytotoxicity and efficacy regarding the reversal of multidrug resistance toward SN-38 and mitoxantrone were explored. The most potent compounds were able to reverse the resistance toward the cytostatic agents with EC50 values below 20 nM. Additionally, the type of interaction between inhibitors and the ABCG2 substrate Hoechst 33342 was investigated yielding competitive and non-competitive interactions suggesting different modes of binding. Finally the effect of the derivatives on vanadate-sensitive ATPase activity of ABCG2 was determined. According to the different effects on ATPase activity we conclude the existence of different binding sites. This study provides the structural requirements for high potency inhibition and elucidates the interaction with ABCG2 setting the basis for further studies.
Magnetic nanoparticle-supported DABCO tribromide: A versatile nanocatalyst for the synthesis of quinazolinones and benzimidazoles and protection/deprotection of hydroxyl groups
Rostami, Amin,Pourshiani, Omid,Navasi, Yahya,Darvishi, Neda,Saadati, Shaghayegh
, p. 9033 - 9040 (2017/08/29)
1,4-Diazabicyclo[2.2.2]octane tribromide supported on magnetic Fe3O4 nanoparticles (MNPs-DABCO tribromide) as a novel heterogeneous tribromide type compound was found to be an efficient and reusable nanocatalyst for the one-pot synthesis of 2-arylquinazolin-4(3H)-ones and 2-aryl-1H-benzo[d]imidazoles through oxidative cyclization of aldehydes with 2-aminobenzamides and 1,2-phenylenediamine, respectively. Also, MNPs-DABCO tribromide catalyzed trimethylsilylation/tetrahydropyranylation and desilylation/depyranylation of a wide variety of alcohols and phenols through changing the solvent medium at room temperature.
