European Journal of Chemistry 2011, 2(2), 193-199 | doi: https://doi.org/10.5155/eurjchem.2.2.193-199.282 | Get rights and content

Issue cover





  Open Access OPEN ACCESS | Open Access PEER-REVIEWED | RESEARCH ARTICLE | DOWNLOAD PDF | VIEW FULL-TEXT PDF | TOTAL VIEWS

Synthesis, antimicrobial and antioxidant activities of 1-(1,4-benzodioxane-2-carbonyl)piperazine derivatives


Lingappa Mallesha (1) , Kikkeri Narasimhasetty Mohana (2,*)

(1) Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570006, India
(2) Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570006,
(*) Corresponding Author

Received: 14 Sep 2010 | Revised: 09 May 2011 | Accepted: 05 Jan 2011 | Published: 30 Jun 2011 | Issue Date: June 2011

Abstract


A series of novel 1-(1,4-benzodioxane-2-carbonyl)piperazine derivatives (6a-h) and (7a-e) were synthesized by nucleophilic substitution reaction of 1-(1,4-benzodioxane-2-carbonyl)piperazine (3) with various sulfonyl and acid chlorides. The newly synthesized compounds were characterized by elemental analyses, UV-visible, FT-IR, 1H NMR and LC-MS spectral studies. All compounds were evaluated for in vitro antibacterial, antifungal and antioxidant activities. Compound, 4-(2-trifluoromethyl)-benzenesulfonyl-1-(1,4-benzodioxane -2-carbonyl)piperazine (6b) exhibited significant antimicrobial activity against tested pathogenic bacterial and fungal strains. Compound, 4-(3-methoxy)-benzoyl-1-(1,4-benzodioxane-2-carbonyl)piperazine (7a) showed moderate antioxidant activity compared to standard drug by 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay method.

2_2_193_199_800


Announcements


Our editors have decided to support scientists to publish their manuscripts in European Journal of Chemistry without any financial constraints.

1- The article processing fee will not be charged from the articles containing the single-crystal structure characterization or a DFT study between September 15, 2023 and October 31, 2023 (Voucher code: FALL2023).

2. A 50% discount will be applied to the article processing fee for submissions made between September 15, 2023 and October 31, 2023 by authors who have at least one publication in the European Journal of Chemistry (Voucher code: AUTHOR-3-2023).

3. Young writers will not be charged for the article processing fee between September 15, 2023 and October 31, 2023 (Voucher code: YOUNG2023).

Editor-in-Chief
European Journal of Chemistry

Keywords


1-(1,4-Benzodioxane-2-carbonyl)piperazine; Antimicrobial activity; Antioxidant activity; Structure-activity relationship; Sulphonyl chlorides; Acid chlorides

Full Text:

PDF
PDF    Open Access

DOI: 10.5155/eurjchem.2.2.193-199.282

Links for Article


| | | | | | |

| | | | | | |

| | | |

Related Articles




Article Metrics

icon graph This Abstract was viewed 2480 times | icon graph PDF Article downloaded 1941 times

Funding information


University Grants Commission, New Delhi, India

Citations

/


[1]. Ravi Ranjan Kumar, Bhaskar Sahu, Shelly Pathania, Pankaj Kumar Singh, M. Jawaid Akhtar, Bhupinder Kumar
Piperazine, a Key Substructure for Antidepressants: Its Role in Developments and Structure‐Activity Relationships
ChemMedChem  16(12), 1878, 2021
DOI: 10.1002/cmdc.202100045
/

[2]. Weijie Si, Tao Zhang, Lanxiang Zhang, Xiangdong Mei, Mengya Dong, Kaixin Zhang, Jun Ning
Design, synthesis and bioactivity of novel phthalimide derivatives as acetylcholinesterase inhibitors
Bioorganic & Medicinal Chemistry Letters  26(9), 2380, 2016
DOI: 10.1016/j.bmcl.2015.07.052
/

[3]. Adrian Olszewski, Kinga Wzgarda-Raj
Pyrazine-2(1H)-thione
IUCrData  6(10), , 2021
DOI: 10.1107/S2414314621011020
/

[4]. Habibullah Khalilullah, Shamshir Khan, Md. Shivli Nomani, Bahar Ahmed
Synthesis, characterization and antimicrobial activity of benzodioxane ring containing 1,3,4-oxadiazole derivatives
Arabian Journal of Chemistry  9, S1029, 2016
DOI: 10.1016/j.arabjc.2011.11.009
/

[5]. Semih Gorduk
Octa-substituted metallophthalocyanines bearing (2,3-dihydrobenzo-1,4-benzodioxin-2-yl)methoxy and chloro groups: Synthesis, characterization and photophysicochemical studies
Journal of Porphyrins and Phthalocyanines  24(04), 548, 2020
DOI: 10.1142/S1088424620500030
/

[6]. C. Shalini, N. Dharmaraj, Nattamai S.P. Bhuvanesh, M.V. Kaveri
Suzuki Miyaura cross-coupling of 2-chloropyrazine with arylboronic acids catalyzed by novel palladium(II) ONO pincer complexes
Inorganica Chimica Acta  540, 121028, 2022
DOI: 10.1016/j.ica.2022.121028
/

[7]. C. Mallikarjunaswamy, L. Mallesha, D.G. Bhadregowda, Othbert Pinto
Studies on synthesis of pyrimidine derivatives and their antimicrobial activity
Arabian Journal of Chemistry  10, S484, 2017
DOI: 10.1016/j.arabjc.2012.10.008
/

[8]. Juan Sun, Cui‐Ping Zhang, Chong‐Hao Chen, Xiao‐Meng Guo, Cai‐Shi Liu, Yang Zhou, Fu‐Liang Hu
Design, Synthesis and Molecular Docking of 1,3,4‐Oxadiazole‐2(3H)‐thione Derivatives Containing 1,4‐Benzodioxane Skeleton as Potential FabH Inhibitors
Chemistry & Biodiversity  20(2), , 2023
DOI: 10.1002/cbdv.202201060
/

[9]. Archana Archana
Synthesis of Novel Triazolyl/Oxadiazolyl/Thiadiazolyl-Piperazine as Potential Anticonvulsant Agents
Drug Research  71(04), 199, 2021
DOI: 10.1055/a-1291-7554
/

[10]. Andrew Toyi Banyikwa, Stephen E. Miller, Richard A. Krebs, Yuewu Xiao, Jeffrey M. Carney, Mark S. Braiman
Anhydrous Monoalkylguanidines in Aprotic and Nonpolar Solvents: Models for Deprotonated Arginine Side Chains in Membrane Environments
ACS Omega  2(10), 7239, 2017
DOI: 10.1021/acsomega.7b00281
/

[11]. Chenna Krishna Reddy Reddivari, Subba Rao Devineni, Jyothi Kumar Malaka Venkateshwarulu, Vijaya Bhaskar Baki, Appa Rao Chippada, Rajendra Wudayagiri, Rami Reddy Yallala Venkata, Naga Raju Chamarthi
ZnBr2-SiO2 catalyzed green synthesis of tetrazoles: Molecular docking and antioxidant activity studies
European Journal of Chemistry  8(1), 66, 2017
DOI: 10.5155/eurjchem.8.1.66-75.1515
/

[12]. Akash Jain, Jasmine Chaudhary, Harpreet Khaira, Bhawna Chopra, Ashwani Dhingra
Piperazine: A Promising Scaffold with Analgesic and Anti-inflammatory Potential
Drug Research  71(02), 62, 2021
DOI: 10.1055/a-1323-2813
/

[13]. Ümit Demirbaş, Duygu Akyüz, Hakkı Türker Akçay, Atıf Koca, Halit Kantekin
Non-peripherally tetra substituted phthalocyanines bearing benzodioxane moieties: Synthesis, characterization and investigation of electrochemical and spectroelectrochemical properties
Journal of Molecular Structure  1189, 234, 2019
DOI: 10.1016/j.molstruc.2019.04.031
/

[14]. Ümit Demirbaş, İpek Ömeroğlu, Hakkı Türker Akçay, Mahmut Durmuş, Halit Kantekin
Synthesis, characterization, photophysical and photochemical properties of peripherally tetra benzodioxane substituted metal-free phthalocyanine and its zinc(II) and magnesium(II) derivatives
Journal of Molecular Structure  1223, 128992, 2021
DOI: 10.1016/j.molstruc.2020.128992
/

[15]. Salama A. Ouf, Sobhi M. Gomha, Mohamed Eweis, Ahmed S. Ouf, Ihab A. A. Sharawy, Sulaiman A. Alharbi
Antidermatophytic activity of some newly synthesized arylhydrazonothiazoles conjugated with monoclonal antibody
Scientific Reports  10(1), , 2020
DOI: 10.1038/s41598-020-77829-x
/

[16]. Mushtaq Ahmad, Zahida Perveen, Adailton J. Bortoluzzi, Shahid Hameed, Muhammad R. Shah, Muhammad Tariq, Ghias ud Din, Muhammad T. Jan, Muhammad Siddique, Muhammad Anwar
Synthesis and characterization of novel iminobenzoates with terminal pyrazine moieties
Chemistry Central Journal  12(1), , 2018
DOI: 10.1186/s13065-018-0396-3
/

[17]. Sandhya Chhakra, A. Mukherjee, H.L. Singh, Suresh Singh Chauhan
Synthesis of Novel Substituted 1,5-Benzothiazepines Containing 1,4-Benzodioxane Sulfonyl Moiety
Asian Journal of Organic & Medicinal Chemistry  4(2), 70, 2019
DOI: 10.14233/ajomc.2019.AJOMC-P159
/

[18]. Poonam Meena, Apra Manral, Vikas Saini, Manisha Tiwari
Protective Effects of a Piperazine Derivative [N-{4-[4-(2-methoxy-phenyl)-piperazin-1-yl]-phenyl} Carbamic Acid Ethyl Ester] Against Aluminium-Induced Neurotoxicity: Insights From In Silico and In Vivo Studies
Neurotoxicity Research  27(3), 314, 2015
DOI: 10.1007/s12640-014-9499-3
/

[19]. Naveen Kumar Kottakki, Soujanya Kumari P V D, Gopi G, Amperayani Karteek Rao, Devi Parimiuma
SYNTHESIS AND ANTIBACTERIAL ACTIVITY OF PIPERAZINE ANALOGUES CONTAINING [1, 3, 4]-OXADIAZOLE RING
INDIAN DRUGS  57(01), 19, 2020
DOI: 10.53879/id.57.01.12165
/

[20]. Shaheen Begum, M.S. Rashida Anjum, G. Poojitha Harisree, N. Sivalakshmi, P. Priyanka, K. Bharathi
Antioxidant Activity of Piperazine Compounds: A Brief Review
Asian Journal of Chemistry  32(9), 2105, 2020
DOI: 10.14233/ajchem.2020.22832
/

[21]. A. B. Sargsyan, A. S. Avakyan, S. O. Vartanyan, G. M. Stepanyan, R. V. Paronikyan
Synthesis of New 1,4-Benzodioxanуl-1,2,4-triazole Derivatives
Russian Journal of General Chemistry  88(4), 839, 2018
DOI: 10.1134/S1070363218040345
/

[22]. M.K. Hema, R.R. ArunRenganathan, S. Nanjundaswamy, C.S. Karthik, Yasser Hussein Issa Mohammed, Saad Alghamdi, N.K. Lokanath, V. Ravishankar Rai, S. Nagashree, P. Mallu
N-(4-bromobenzylidene)-2,3-dihydrobenzo[b][1,4]dioxin-6-amine: Synthesis, crystal structure, docking and in-vitro inhibition of PLA2
Journal of Molecular Structure  1218, 128441, 2020
DOI: 10.1016/j.molstruc.2020.128441
/

[23]. Donka Rajasekhar, Doddaga Srinivasulu, Chenchugari Sridhar, Godlaveti Vijay Narasimha Kumar, Peddakonda Ramesh
Synthesis, Spectral Characterization and Antioxidant Activity of Novel Zafirlukast Sulfonyl Derivatives
Journal of the Chinese Chemical Society  63(3), 267, 2016
DOI: 10.1002/jccs.201500143
/

[24]. Gulraiz Ahmad, Nasir Rasool, Adeel Mubarik, Ameer Fawad Zahoor, Muhammad Ali Hashmi, Muhammad Zubair, Muhammad Bilal, Mohamed Hussien, Muhammad Saeed Akhtar, Sajjad Haider
Facile Synthesis of 5-Aryl-N-(pyrazin-2-yl)thiophene-2-carboxamides via Suzuki Cross-Coupling Reactions, Their Electronic and Nonlinear Optical Properties through DFT Calculations
Molecules  26(23), 7309, 2021
DOI: 10.3390/molecules26237309
/

[25]. Kavitha Raj Varadaraju, Jajur Ramanna Kumar, Lingappa Mallesha, Archana Muruli, Kikkeri Narasimha Shetty Mohana, Chethan Kumar Mukunda, Umesha Sharanaiah
Virtual Screening and Biological Evaluation of Piperazine Derivatives as Human Acetylcholinesterase Inhibitors
International Journal of Alzheimer's Disease  2013, 1, 2013
DOI: 10.1155/2013/653962
/

[26]. M. A. Abbasi, S. Tariq, Aziz-ur-Rehman, S. Z. Siddiqui, I. Ahmad, R. Malik, S. A. A. Shah
Synthesis of some new N-substituted-N-(2,3-Dihydro-[1,4]benzodioxin-6-yl)-4-acetamidobenzenesulfonamides as valuable antibacterial agents
Russian Journal of Bioorganic Chemistry  42(2), 198, 2016
DOI: 10.1134/S1068162016020023
/

References


[1]. Bolognesi, M. L.; Budriesi, R.; Cavalli, A.; Chiarini, A.; Gotti, R.; Leonardi, A.; Minarini, A.; Poggesi, E.; Recanatini, M.; Rosini, M.; Tummiatti, V.; Melchiorre, C. J. Med. Chem. 1999, 42, 4214-4224.
doi:10.1021/jm991065j
PMid:10514291

[2]. Cantuti-Castelvetri, I.; Shukitt-Hale, B.; Joseph, J. A. Int. J. Dev. Neurosci. 2000, 18, 367-381.
doi:10.1016/S0736-5748(00)00008-3

[3]. Vaya, J.; Aviram, M. Curr. Med. Chem.-Immunol. Endocr. Metab. Agents 2001, 1, 99-117.
doi:10.2174/1568013013359168

[4]. Blokhina, O.; Virolainen, E.; Fagerstedt, K. V. Ann. Bot. 2003, 91, 179-194.
doi:10.1093/aob/mcf118
PMid:12509339

[5]. Hollman, P. C. H.; Katan, M. B. Food Chem. Toxicol. 1999, 37, 937-942.
doi:10.1016/S0278-6915(99)00079-4

[6]. Berkheij, M. Tetrahedron Lett. 2005, 46, 2369-2371.
doi:10.1016/j.tetlet.2005.02.085

[7]. Upadhayaya, R. S.; Sinha, N.; Jain, S.; Kishore, N.; Chandra, R.; Arora, S. K. Bioorg. Med. Chem. 2004, 12, 2225-2238.
doi:10.1016/j.bmc.2004.02.014

[8]. Choudhary, P.; Kumar, R.; Verma, A. K.; Singh, D. Bioorg. Med. Chem. 2006, 14, 1819-1826.
doi:10.1016/j.bmc.2005.10.032

[9]. Rossen, K.; Weissman, S. A.; Sager, J.; Reamer, R. A.; Askin, D.; Volante, R. P.; Reider, P. J. Tetrahedron Lett. 1995, 36, 6419-6422.
doi:10.1016/0040-4039(95)01345-I

[10]. Amin, E. A.; Welsh, W. J. J. Med. Chem. 2003, 44, 3849-3855.
doi:10.1021/jm010236t

[11]. Torisu, K.; Kobayashi, K.; Iwahashi, M.; Nakai, Y.; Onoda, T.; Nagase, T.; Sugimoto, I.; Okada, Y.; Matsumoto, R.; Nanbu, F.; Ohuchida, S.; Nakai, H.; Toda, M. Bioorg. Med. Chem. 2004, 12, 5361-5378.
doi:10.1016/j.bmc.2004.07.048

[12]. Bolchi, C.; Pallavicini, M.; Fumagalli, L.; Marchini, N.; Moroni, B.; Rusconi, C.; Valoti, E. Tetrahedron: Asymmetry 2005, 16, 1639-1643.
doi:10.1016/j.tetasy.2005.01.052

[13]. Marchini, N.; Bombieri, G.; Artali, R.; Bolchi, C.; Pallavicini, M.; Valoti, E. Tetrahedron: Asymmetry 2005, 16, 2099-2106.
doi:10.1016/j.tetasy.2005.05.010

[14]. Fang, Q. K.; Grover, P.; Han, Z.; McConville, F. X.; Rossi, R. F.; Olsson, D. J.; Kessler, D. W.; Wald, S. A.; Senanayake, C. H. Tetrahedron: Asymmetry 2001, 12, 2169-2174.
doi:10.1016/S0957-4166(01)00368-8

[15]. Yasuda, G.; Hasegawa, K.; Kuji, T.; Ogawa, N.; Shimura, G.; Umemura, S.; Tochikubo, O. Diabet. Med. 2005, 22, 1394-1400.
doi:10.1111/j.1464-5491.2005.01636.x
PMid:16176202

[16]. Grcman, M.; Vrecer, F.; Meden, A. J. Therm. Anal. Cal. 2002, 68, 373-387.
doi:10.1023/A:1016019214704

[17]. Sohn, Y. T.; Lee, Y. H. Arch. Pharm. Res. 2005, 28, 730-735.
doi:10.1007/BF02969365
PMid:16042084

[18]. Bolchi, C.; Fumagalli, L.; Moroni, B.; Pallavicini, M.; Valoti, E. Tetrahedron: Asymmetry 2003, 14, 2247-2251.
doi:10.1016/j.tetasy.2003.09.012

[19]. Bauer, A. W.; Kirby, W. M.; Sherris, J. C.; Turck, M. Am. J. Clin. Pathol. 1966, 45, 493-496.
PMid:5325707

[20]. Satish, S.; Mohana, D. C.; Raghavendra, M. P.; Raveesha, K. A. J. Agric. Technol. 2007, 3, 109-119.

[21]. Shih, M. H.; Ke, F. Y. Bioorg. Med. Chem. 2004, 12, 4633-4643.
doi:10.1016/j.bmc.2004.06.033

[22]. Gulcin, I.; Beydemir, S; Alici, H. A.; Elmastas, M.; Buyukokuroglu, M. E. Pharmacol. Res. 2004, 49, 59-66.
doi:10.1016/j.phrs.2003.07.012

[23]. Elmastas, M.; Gulcin, I.; Beydemir, S.; Kufrevioglu, O. I.; Aboul-Enein, H. Y. Anal. Lett. 2006, 39, 47-65.
doi:10.1080/00032710500423385

[24]. Hadi, J. S.; Alsalami, B. K.; Essa, A. H. J. Sci. Res. 2009, 1, 563-568.

[25]. Shafiee, A.; Emami, S.; Ghodsi, S.; Najjari, S.; Sorkhi, M.; Samadi, N.; Faramarzi, M. A.; Foroumadi, A. J. Iran. Chem. Soc. 2009, 6, 325-333.

[26]. Roopan, S. M.; Khan, F. N. Arkivoc 2009, 13, 161-169.


How to cite


Mallesha, L.; Mohana, K. Eur. J. Chem. 2011, 2(2), 193-199. doi:10.5155/eurjchem.2.2.193-199.282
Mallesha, L.; Mohana, K. Synthesis, antimicrobial and antioxidant activities of 1-(1,4-benzodioxane-2-carbonyl)piperazine derivatives. Eur. J. Chem. 2011, 2(2), 193-199. doi:10.5155/eurjchem.2.2.193-199.282
Mallesha, L., & Mohana, K. (2011). Synthesis, antimicrobial and antioxidant activities of 1-(1,4-benzodioxane-2-carbonyl)piperazine derivatives. European Journal of Chemistry, 2(2), 193-199. doi:10.5155/eurjchem.2.2.193-199.282
Mallesha, Lingappa, & Kikkeri Narasimhasetty Mohana. "Synthesis, antimicrobial and antioxidant activities of 1-(1,4-benzodioxane-2-carbonyl)piperazine derivatives." European Journal of Chemistry [Online], 2.2 (2011): 193-199. Web. 10 Dec. 2023
Mallesha, Lingappa, AND Mohana, Kikkeri. "Synthesis, antimicrobial and antioxidant activities of 1-(1,4-benzodioxane-2-carbonyl)piperazine derivatives" European Journal of Chemistry [Online], Volume 2 Number 2 (30 June 2011)

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.2.2.193-199.282


CrossRef | Scilit | GrowKudos | Researchgate | Publons | ScienceGate | Scite | Lens | OUCI

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

ZoteroSave to Zotero MendeleySave to Mendeley



European Journal of Chemistry 2011, 2(2), 193-199 | doi: https://doi.org/10.5155/eurjchem.2.2.193-199.282 | Get rights and content

Refbacks

  • There are currently no refbacks.


Bookmark and Share


Copyright (c)




© Copyright 2010 - 2023 • 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 2010-2023 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.