European Journal of Chemistry 2017, 8(4), 349-357 | doi: https://doi.org/10.5155/eurjchem.8.4.349-357.1637 | Get rights and content






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

Molecular self-assembly in indole-based benzamide derivative: Crystal structure, Hirshfeld surfaces and antimicrobial activity


Ilkay Gumus (1,*) orcid , Ummuhan Solmaz (2) orcid , Serpil Gonca (3) orcid , Hakan Arslan (4) orcid

(1) Department of Chemistry, Faculty of Arts and Science, Mersin University, Mersin, TR 33343, Turkey
(2) Department of Chemistry, Faculty of Arts and Science, Mersin University, Mersin, TR 33343, Turkey
(3) Department of Pharmaceutical Microbiology, Faculty of Pharmacy, Mersin University, Mersin, TR 33343, Turkey
(4) Department of Chemistry, Faculty of Arts and Science, Mersin University, Mersin, TR 33343, Turkey
(*) Corresponding Author

Received: 12 Oct 2017 | Revised: 28 Oct 2017 | Accepted: 28 Oct 2017 | Published: 31 Dec 2017 | Issue Date: December 2017

Abstract


Two new compounds, 1H-indole-7-amine (1) and N-(1H-indol-7-yl)-2-methylbenzamide (2) were synthesized and structurally characterized by NMR and FT-IR spectroscopic techniques. The molecular structure of compound 2 was further elucidated by single-crystal X-ray diffraction technique. Moreover, the crystal packing of compound 2 is analyzed in terms of non-covalent N-H···O, C-H···π, and parallel displaced π···π interactions. Hirshfeld surface analysis and decomposed fingerprint plots of the compound 2 were performed to visualize the presence of strong hydrogen bond N-H···O and C-H···π stacking interactions. Hirshfeld surface analysis and decomposed fingerprint plots show that the structure of compound 2 is stabilized by H···H, N-H···O, C-H···π and π···π intermolecular interactions and these interactions contribute mostly to molecular self-assembly in the crystal. In addition, compound 2 was evaluated for both their in-vitro antibacterial and antifungal activity. The obtained results have been reported, explained and compared with fluconazole and ampicillin used as reference drugs.


Keywords


Antimicrobial activity; Single crystal structure; Molecular self-assembly; Hirshfeld surface analysis; Deformation electron density; Indole-based benzamide derivative

Full Text:

PDF /    /


DOI: 10.5155/eurjchem.8.4.349-357.1637

Links for Article


| | | | | | |

| | | | | | |

Related Articles




Article Metrics

This Abstract was viewed 990 times | PDF Article downloaded 219 times

Funding information


This work was supported by Mersin University Research Fund [Project No: 2015-AP4-1162].

Citations

/


[1]. Ilkay Gumus, Ummuhan Solmaz, Gun Binzet, Ebru Keskin, Birdal Arslan, Hakan Arslan
Supramolecular self-assembly of new thiourea derivatives directed by intermolecular hydrogen bonds and weak interactions: crystal structures and Hirshfeld surface analysis
Research on Chemical Intermediates  45(2), 169, 2019
DOI: 10.1007/s11164-018-3596-5
/


[2]. Ebru Keskin, Ummuhan Solmaz, Gun Binzet, Ilkay Gumus, Hakan Arslan
Synthesis, characterization and crystal structure of platinum(II) complexes with thiourea derivative ligands
European Journal of Chemistry  9(4), 360, 2018
DOI: 10.5155/eurjchem.9.4.360-368.1774
/


References

[1]. Barluenga, J.; Valdes, C. Mod. Heterocycl. Chem. 2011, 1, 377-531.
https://doi.org/10.1002/9783527637737.ch5

[2]. Chadha, N.; Silakari, O. Eur. J. Med. Chem. 2017, 134, 159-184.
https://doi.org/10.1016/j.ejmech.2017.04.003

[3]. Baeyer, A.; Emmerling, A. Ber. Dtsch. Chem. Ges. 1869, 2, 679-682.
https://doi.org/10.1002/cber.186900201268

[4]. Joule, J. A. 'Indoles' in 'Science of Synthesis'; Thomas, E. J., Ed.; Georg Thieme: Stuttgart, New York, 2011; Vol. 10 Knowledge Update 2010/2, pp. 526.

[5]. Faulkner, D. J. Nat. Prod. Rep. 2001, 18, 1-49.
https://doi.org/10.1039/b006897g

[6]. Chelucci, G. Coord. Chem. Rev. 2017, 331, 37-53.
https://doi.org/10.1016/j.ccr.2016.09.014

[7]. Sharma, V.; Kumar, P.; Pathak, D. J. Heterocycl. Chem. 2010, 47, 491-502.

[8]. Kaushik, N. K.; Kaushik, N.; Attri, P.; Kumar, N.; Kim, C. H.; Verma, A. K.; Choi, E. H. Molecules 2013, 18, 6620-6662.
https://doi.org/10.3390/molecules18066620

[9]. Suzen, S.; Buyukbingol, E. Il Farmaco 2000, 55, 246-248.
https://doi.org/10.1016/S0014-827X(00)00028-8

[10]. Buyukbingol, E.; Suzen, S.; Klopman, G. Il Farmaco 1994, 49, 443-447.

[11]. Pojarova, M.; Kaufmann, D.; Gastpar, R.; Nishino, T.; Reszka, P.; Bednarskib, P. J.; Angerer, E. V. Med. Chem. 2007, 15, 7368-7379.
https://doi.org/10.1016/j.bmc.2007.07.046

[12]. Morteza, S.; Mohammad, A. Z.; Hendrik, G. K.; Zahra, T. Chem. Rev. 2010, 110, 2250-2293.
https://doi.org/10.1021/cr900195a

[13]. Chyan, Y. J.; Poeggler, B.; Omar, R. A.; Chain, D. G.; Frangione, B.; Ghiso, J.; Pappolla, M. A. J. Biol. Chem. 1999, 274, 21937-21942.
https://doi.org/10.1074/jbc.274.31.21937

[14]. Suzen, S.; Buyukbingol, E. Il Farmaco 1998, 53, 525-527.
https://doi.org/10.1016/S0014-827X(98)00053-6

[15]. Darehkordi, A.; Rahmani, F.; Hashemi V. Tetrahedron Lett. 2013, 54, 4689-4692.
https://doi.org/10.1016/j.tetlet.2013.06.093

[16]. Srivastava, N.; Banik, B. K. J. Org. Chem. 2003, 68, 2109-2114.
https://doi.org/10.1021/jo026550s

[17]. Shimazakia, Y.; Yajimab, T.; Takanic, M.; Yamauchi, O. Coord. Chem. Rev. 2009, 253, 479-492.
https://doi.org/10.1016/j.ccr.2008.04.012

[18]. Kordic, B.; Kovacevic, M.; Sloboda, T.; Vidovic A.; Jovic, B. J. Mol. Struct. 2017, 1144, 159-165.
https://doi.org/10.1016/j.molstruc.2017.05.035

[19]. Nocek, J. M.; Zhou, J. S.; De Forest, S.; Priyadarshy, S.; Beratan, D. N.; Onuchic, J. N.; Hoffman, B. M. Chem. Rev. 1996, 96, 2459-2489.
https://doi.org/10.1021/cr9500444

[20]. Dougherty, D. A. Science 1996, 271, 163-168.
https://doi.org/10.1126/science.271.5246.163

[21]. Ma, J. C.; Dougherty, D. A. Chem. Rev. 1997, 97, 1303-1324.
https://doi.org/10.1021/cr9603744

[22]. Gallivan, J. P.; Dougherty, D. A. Proc. Natl. Acad. Sci. USA 1999, 96, 9459-9464.
https://doi.org/10.1073/pnas.96.17.9459

[23]. Dolomanov, O. V.; Bourhis, L. J.; Gildea, R. J.; Howard, J. A. K.; Puschmann, H. J. Appl. Cryst. 2009, 42, 339-341.
https://doi.org/10.1107/S0021889808042726

[24]. Palatinus, L.; Chapuis, G. J. Appl. Cryst. 2007, 40, 786-790.
https://doi.org/10.1107/S0021889807029238

[25]. Palatinus, L.; VanderLee, A. J. Appl. Cryst. 2008, 41, 975-984.
https://doi.org/10.1107/S0021889808028185

[26]. Palatinus, L.; Prathapa, S. J.; VanSmaalen, S. J. Appl. Cryst. 2012, 45, 575-580.
https://doi.org/10.1107/S0021889812016068

[27]. Sheldrick, G. M. Acta Cryst. C 2015, 71, 3-8.
https://doi.org/10.1107/S2053229614024218

[28]. Zielinski, T.; Dydio, P.; Jurczak, J. Tetrahedron 2008, 64, 568-574.
https://doi.org/10.1016/j.tet.2007.11.012

[29]. Turner, M. J.; McKinnon, J. J.; Wolff, S. K.; Grimwood, D. J.; Spackman, P. R.; Jayatilaka, D.; Spackman, M. A. CrystalExplorer17, University of Western Australia, 2017.

[30]. Burlesson, F. G.; Chambers, T. M.; Wedbrauk, D. L. Virology. A Laboratory Manual, Academic Press, New York, 1992.

[31]. National Committee for Clinical Laboratory Standards. Reference method for broth dilution antifungal susceptibility testing of yeasts. Approved standard NCCLS document M27-A. National Committee for Clinical Laboratory Standards, Wayne, Pa., (2002).

[32]. Arslan, H.; Duran, N.; Borekci, G.; Ozer, C. K.; Akbay, C. Molecules 2009, 14, 519‐527.
https://doi.org/10.3390/molecules14010519

[33]. Planas J. G.; Masalles, C.; Sillanpa, R.; Kivekas, R.; Teixidor, F.; Vinas, C. Cryst. Eng. Comm. 2006, 8, 75-83.

Supporting information


The Supplementary Material for this article can be found online at: Supplementary files

How to cite


Gumus, I.; Solmaz, U.; Gonca, S.; Arslan, H. Eur. J. Chem. 2017, 8(4), 349-357. doi:10.5155/eurjchem.8.4.349-357.1637
Gumus, I.; Solmaz, U.; Gonca, S.; Arslan, H. Molecular self-assembly in indole-based benzamide derivative: Crystal structure, Hirshfeld surfaces and antimicrobial activity. Eur. J. Chem. 2017, 8(4), 349-357. doi:10.5155/eurjchem.8.4.349-357.1637
Gumus, I., Solmaz, U., Gonca, S., & Arslan, H. (2017). Molecular self-assembly in indole-based benzamide derivative: Crystal structure, Hirshfeld surfaces and antimicrobial activity. European Journal of Chemistry, 8(4), 349-357. doi:10.5155/eurjchem.8.4.349-357.1637
Gumus, Ilkay, Ummuhan Solmaz, Serpil Gonca, & Hakan Arslan. "Molecular self-assembly in indole-based benzamide derivative: Crystal structure, Hirshfeld surfaces and antimicrobial activity." European Journal of Chemistry [Online], 8.4 (2017): 349-357. Web. 31 May. 2020
Gumus, Ilkay, Solmaz, Ummuhan, Gonca, Serpil, AND Arslan, Hakan. "Molecular self-assembly in indole-based benzamide derivative: Crystal structure, Hirshfeld surfaces and antimicrobial activity" European Journal of Chemistry [Online], Volume 8 Number 4 (31 December 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.8.4.349-357.1637

| | | | | | |

| | | | | |

Save to Zotero Save to Mendeley



European Journal of Chemistry 2017, 8(4), 349-357 | doi: https://doi.org/10.5155/eurjchem.8.4.349-357.1637 | Get rights and content

Refbacks

  • There are currently no refbacks.




Copyright (c) 2017 Authors

License URL: http://eurjchem.com/index.php/eurjchem/pages/view/terms


© Copyright 2010 - 2020  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 2010-2020 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.

hatay escort hatay escort corlu escort corum escort burgaz escort giresun escort aydin escort ordu escort erzincan escort hatay escort sivas escort rize escort edirne escort aksaray escort kibris escort isparta escort erzurum escort tekirdag escort usak escort urfa escort kastamonu escort kibris escort manisa escort giresun escort urfa escort nevsehir escort sivas escort yalova escort ordu escort hatay escort yalova escort amasya escort kayseri escort ordu escort maras escort canakkale escort yalova escort balikesir escort manisa escort urfa escort mugla escort trabzon escort bolu escort corlu escort diyarbakir escort isparta escort kutahya escort elazig escort erzurum escort sakarya escort afyon escort kutahya escort konya escort agri escort cesme escort sinop escort sivas escort konya escort kibris escort adapazari escort luleburgaz escort adana escort kibris escort rize escort sakarya escort alanya escort isparta escort burdur escort konya escort bitlis escort canakkale escort sivas escort amasya escort mus escort aydin escort van escort yalova escort kastamonu escort mardin escort bolu escort afyon escort sakarya escort isparta escort tokat escort trakya escort bayburt escort urfa escort mardin escort