European Journal of Chemistry 2017, 8(3), 317-320 | doi: https://doi.org/10.5155/eurjchem.8.3.317-320.1586 | Get rights and content

Issue cover





  Open Access OPEN ACCESS | Open Access PEER-REVIEWED | SHORT COMMUNICATION | DOWNLOAD PDF | VIEW FULL-TEXT PDF | TOTAL VIEWS

Synthesis of quinazolinones derivatives an antiproliferative agent against human lung carcinoma cells


Satish Uttamrao Deshmukh (1) , Kiran Ramesh Kharat (2) , Gajanan Gulabrao Kadam (3) , Rajendra Pundlikrao Pawar (4,*)

(1) Department of Chemistry, Deogiri College, Aurangabad, 431005 (MS), India
(2) Department of Biotechnology, Deogiri College, Aurangabad, 431005 (MS), India
(3) Department of Chemistry, Shri Datta Arts, Commerce and Science College, Hadgaon, 431712 (MS), India
(4) Department of Chemistry, Deogiri College, Aurangabad, 431005 (MS), India
(*) Corresponding Author

Received: 20 May 2017 | Revised: 31 Jul 2017 | Accepted: 05 Aug 2017 | Published: 30 Sep 2017 | Issue Date: September 2017

Abstract


2,3‐Dihydroquinazolin‐4(1H)‐one derivatives (3a-p) were synthesized in excellent yields. These compounds were screened for antiproliferative activity against A549 cells and were found as potent cytotoxicity. Compounds A4, A8, A10 found to be more promising antiproliferative against the lung carcinoma A549 cells. IC50 values for compounds A4, A8 and A10 were found to be 8.6, 8.9 and 8.1 μg/L against A549 cells, respectively.


Keywords


Ionic liquid; Green chemistry; 2-Aminobenzamide; Antiproliferative activity; Lung carcinoma A549 cells; 2,3‐Dihydroquinazolin‐4(1H)‐one

Full Text:

PDF
PDF    Open Access

DOI: 10.5155/eurjchem.8.3.317-320.1586

Links for Article


| | | | | | |

| | | | | | |

| | | |

Related Articles




Article Metrics

icon graph This Abstract was viewed 1105 times | icon graph PDF Article downloaded 312 times


Citations

/


[1]. Siddique A. Ansari, Satish U. Deshmukh, Rajesh B. Patil, Manoj G. Damale, Rajendra H. Patil, Hamad M. Alkahtani, Abdulrahman A. Almehizia, Hanaa M. Al‐Tuwajiri, Fadilah S. Aleanizy, Fulwah Y. Alqahtani, Shahebaaz K. Pathan, Jaiprakash N. Sangshetti
Identification of Promising Biofilm Inhibitory and Cytotoxic Quinazolin‐4‐one Derivatives: Synthesis, Evaluation, Molecular Docking and ADMET Studies
ChemistrySelect  4(12), 3559, 2019
DOI: 10.1002/slct.201803795
/


[2]. Hossein Ghafuri, Nahal Goodarzi, Afsaneh Rashidizadeh, Mohammad Ali Douzandegi Fard
ompg-C3N4/SO3H: an efficient and recyclable organocatalyst for the facile synthesis of 2,3-dihydroquinazolin-4(1H)-ones
Research on Chemical Intermediates  45(10), 5027, 2019
DOI: 10.1007/s11164-019-03873-6
/


[3]. Bi Bi Fatemeh Mirjalili, Zahra Zaghaghi, Aazam Monfared
Synthesis of 2,3‐dihydroquinazolin‐4(1 H )‐ones in the presence of Fe 3 O 4 @nano‐cellulose–OPO 3 H as a bio‐based magnetic nanocatalyst
Journal of the Chinese Chemical Society  67(2), 197, 2020
DOI: 10.1002/jccs.201900264
/


[4]. Bi Bi Fatemeh Mirjalili, Seyedeh Deldar Eliin, Seyede Azita Fazeli-Attar
Synthesis of 2,3-dihydroquinazolinones using nano-ovalbumin as a non-toxic biocatalyst
SN Applied Sciences  2(5), , 2020
DOI: 10.1007/s42452-020-2652-0
/


[5]. Dongping Cheng, Xianhang Yan, Yueqi Pu, Jing Shen, Xiaoliang Xu, Jizhong Yan
2,3‐Dichloro‐5,6‐dicyano‐1,4‐benzoquinone (DDQ)‐Mediated Tandem Oxidative Annulation for Preparing 2,2‐Disubstituted 2,3‐Dihydroquinazolin‐4(1H)‐ones
European Journal of Organic Chemistry  2021(6), 944, 2021
DOI: 10.1002/ejoc.202001479
/


References


[1]. Daniel, A.; Erlanson, R. S.; McDowell, T. J. Med. Chem. 2004, 47, 3463‐3482.
https://doi.org/10.1021/jm040031v

[2]. Mosaad, M. S.; Mohsen, K. M.; Emad, K. M.; Abotaleb, N.; Salwa, N. M.; Marwa, A. F. Acta Pol. Pharm. 2010, 67, 159-171.

[3]. Hour, M. J.; Huang, L. J.; Kuo, S. C.; Xia Y.; Bastow, K.; Nakanishi, Y.; Hamel, E.; Lee, K. H. J. Med. Chem. 2000, 43, 4479-4487.
https://doi.org/10.1021/jm000151c

[4]. Farghaly, A. M.; Soliman, R.; Khalil, M. A.; Bekhit A. A.; El-Din, A.; Bekhit, A. Boll. Chim. Farm. 2002, 141, 372-378.

[5]. Kikuchi, H.; Tasaka, H.; Hirai, S.; Takaya, Y.; Iwabuchi, Y.; Ooi, H.; Hatakeyama, S.; Kim, H. S.; Wataya, Y.; Oshima, Y. J. Med. Chem. 2002, 45, 2563-2570.
https://doi.org/10.1021/jm010448q

[6]. Hour, M. J.; Huang, L. J.; Kuo, S. C.; Xia, Y.; Bastow, K.; Nakanishi, Y.; Hamel, E.; Lee, K. H. J. Med. Chem. 2000, 43, 4479‐4487.
https://doi.org/10.1021/jm000151c

[7]. Birch, H. L.; Buckley, G. M.; Davies, N.; Dyke, H. J.; Frost, E. J.; Gilbert, P. J.; Hannah, D. R.; Haughan, A. F.; Madigan, M. J.; Morgan, T.; Pitt, W. R.; Ratcliffe, A. J.; Ray, N. C.; Richard, M. D.; Sharpe, A.; Taylor, A. J.; Whitworth, J. M.; Williams, S. C. Bioorg. Med. Chem. Lett. 2005, 15, 5335‐5339.
https://doi.org/10.1016/j.bmcl.2005.06.108

[8]. Rexall Drug Co., U. S. Patent, 1966, 3257397.

[9]. Okumura, K.; Oine, T.; Yamada, Y.; Hayashi, G.; Nakama, M. J. Med. Chem. 1968, 11, 348‐351.
https://doi.org/10.1021/jm00308a036

[10]. Shulton Inc., U. S. Patent, 1966, 3265697.

[11]. Hirose, N.; Kuriyama, S.; Sohda, S.; Sakaguchi, K.; Yamamoto, H. Chem. Pharm. Bull. 1973, 21, 1005‐1013.
https://doi.org/10.1248/cpb.21.1005

[12]. Parkanyi, C.; Schmidt, D. S. J. Heterocycle Chem. 2000, 37, 725-729.
https://doi.org/10.1002/jhet.5570370409

[13]. Davoodina, A.; Khashi, M.; Hoseini, N. T. Chin. J. Cat. 2014, 35, 1054-1058.
https://doi.org/10.1016/S1872-2067(14)60041-3

[14]. Cheng, R.; Guo, T.; Zhang-Negrerie, D.; Du, Y.; Zhao, K. Synthesis, 2013, 45, 2998-3006.
https://doi.org/10.1055/s-0033-1338521

[15]. Sharma, M.; Chauhan P. M. S. Chem. Bio. Interface 2013, 3, 116-122.

[16]. Bharate, S. B.; Mupparapu, N.; Manda, S.; Bharate, J. B.; Mudududdla, R.; Yadav, R. R.; Vishwakarma, R. A. Arkivoc 2012, 8, 308-318.

[17]. Yoo, C. L.; Fettinger, J. C.; Kurth, M. J. J. Org. Chem. 2005, 70, 6941-6943.
https://doi.org/10.1021/jo050450f

[18]. Baghbanzadeh, M.; Salehi, P.; Dabiri, M.; Kozehgarya, G. Synthesis 2006, 2, 344-348.

[19]. Karimi, J. Z.; Arjimandi, R. Monatsh. Chem. 2011, 142, 631-635.
https://doi.org/10.1007/s00706-011-0494-6

[20]. Salehi, P.; Dabiri, M.; Zolfigol, M. A.; Baghbanzadeh, M. Synlett. 2005, 7, 1155-1157.
https://doi.org/10.1055/s-2005-865200

[21]. Dabiri, M.; Salehi, P.; Otokesh, S.; Baghbanzadeh, M.; Kozehgarya, G.; Mohammadi, A. A. Tetrahedron Lett. 2005, 46, 6123-6126.
https://doi.org/10.1016/j.tetlet.2005.06.157

[22]. Salehi, P.; Dabiri, M.; Baghbanzadeh, M.; Bahramnejad, M. Synth. Commun. 2006, 36, 2287-2292.
https://doi.org/10.1080/00397910600639752

[23]. Chen, Y.; Shan, W.; Lei, M.; Hua, L. Tetrahedron Lett. 2012, 53, 5923-5925.
https://doi.org/10.1016/j.tetlet.2012.08.090

[24]. Safari, J.; Gandomi-Ravandi, S. J. Mol. Catalysis A: Chem. 2013, 371, 135-140.
https://doi.org/10.1016/j.molcata.2013.01.031

[25]. Rao, A. V. D.; Vykunteswararao, B. P.; Bhaskarkumar, T.; Jogdand, N, R.; Kalita, D.; Lilakar, J. K. D.; Siddaiah, V. Sanasi, P. D.; Raghunad, A. Tetrahedron Lett. 2015, 56(32), 4714-4717.

[26]. Obaiah, O.; Kebbahalli, N. N.; Goravanahalli, R. M.; Chottanahalli, P. S.; Kanchugarakoppal, R. S.; Kempegowda, M. Eur. J. Chem. 2014, 5, 671‐675.
https://doi.org/10.5155/eurjchem.5.4.671-675.1071

[27]. Darvatkar, N. B.; Bhilare, S. V.; Deorukhkar, A.; R; Raut, D. G.; Salunkhe, M. M. Green Chem. Lett. Rev. 2010, 3, 301-306.
https://doi.org/10.1080/17518253.2010.485581

[28]. Dindulkar, S. D.; Oha, J.; Arole; V. M.; Jeong, Y. T. Comp. Rend. Chim. 2014, 17, 971-979.
https://doi.org/10.1016/j.crci.2013.11.008

[29]. Roham, P. H.; Kharat, K. R.; Mungde, P.; Jadhav, M. A.; Makhija, S. J. Nutrition Cancer 2016, 86(2), 305-311.
https://doi.org/10.1080/01635581.2016.1142583


How to cite


Deshmukh, S.; Kharat, K.; Kadam, G.; Pawar, R. Eur. J. Chem. 2017, 8(3), 317-320. doi:10.5155/eurjchem.8.3.317-320.1586
Deshmukh, S.; Kharat, K.; Kadam, G.; Pawar, R. Synthesis of quinazolinones derivatives an antiproliferative agent against human lung carcinoma cells. Eur. J. Chem. 2017, 8(3), 317-320. doi:10.5155/eurjchem.8.3.317-320.1586
Deshmukh, S., Kharat, K., Kadam, G., & Pawar, R. (2017). Synthesis of quinazolinones derivatives an antiproliferative agent against human lung carcinoma cells. European Journal of Chemistry, 8(3), 317-320. doi:10.5155/eurjchem.8.3.317-320.1586
Deshmukh, Satish, Kiran Ramesh Kharat, Gajanan Gulabrao Kadam, & Rajendra Pundlikrao Pawar. "Synthesis of quinazolinones derivatives an antiproliferative agent against human lung carcinoma cells." European Journal of Chemistry [Online], 8.3 (2017): 317-320. Web. 28 Nov. 2021
Deshmukh, Satish, Kharat, Kiran, Kadam, Gajanan, AND Pawar, Rajendra. "Synthesis of quinazolinones derivatives an antiproliferative agent against human lung carcinoma cells" European Journal of Chemistry [Online], Volume 8 Number 3 (30 September 2017)

The other citation formats (EndNote | Reference Manager | ProCite | BibTeX | RefWorks) for this article can be found online at: How to cite item



DOI Link: https://doi.org/10.5155/eurjchem.8.3.317-320.1586

CrossRef | Scilit | GrowKudos | Researchgate | Publons | Microsoft | scibey | Scite | Lens | OUCI

WorldCat Paperbuzz | LibKey Citeas | Dimensions | Semanticscholar | Plumx | Kopernio | Zotero | Mendeley

ZoteroSave to Zotero MendeleySave to Mendeley



European Journal of Chemistry 2017, 8(3), 317-320 | doi: https://doi.org/10.5155/eurjchem.8.3.317-320.1586 | Get rights and content

Refbacks

  • There are currently no refbacks.




Copyright (c)





© Copyright 2010 - 2021  Atlanta Publishing House LLC All Right Reserved.

The opinions expressed in all articles published in European Journal of Chemistry are those of the specific author(s), and do not necessarily reflect the views of Atlanta Publishing House LLC, or European Journal of Chemistry, or any of its employees.

Copyright 2010-2021 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 2850 Smith Ridge Trce Peachtree Cor GA 30071-2636, USA. Registered in USA.