European Journal of Chemistry

Crystallographic structure, activity prediction, and hydrogen bonding analysis of some CSD-based 3,3'-bis-indole derivatives: A review

Article Sidebar

PDF
Published: Dec 31, 2021
DOI: https://doi.org/10.5155/eurjchem.12.4.493-501.2145
Keywords:
Bis-indole, X-ray diffraction, Biological activity, Hydrogen bonding, Geometrical parameters, Bifurcated hydrogen bonds
Section
Review Article
Issue
Vol. 12 No. 4 (2021): December 2021
Dates
Received 2021-07-10
Accepted 2021-08-28
Published 2021-12-31
Crossmark


Main Article Content

Varun Sharma
Department of Physics, University of Jammu, Jammu Tawi-180006, India
https://orcid.org/0000-0003-2866-8638
Goutam Brahmachari
Laboratory of Natural Products and Organic Synthesis, Department of Chemistry, Visva-Bharati (A Central University), Santiniketan-731235, West Bengal, India
https://orcid.org/0000-0001-9925-6281
Vivek Kumar Gupta
Department of Physics, University of Jammu, Jammu Tawi-180006, India
https://orcid.org/0000-0003-2471-5943

Abstract

Herein we report crystallographic comparison of some geometrical and structural features for a series of biologically relevant bis-indole derivatives. Selected bond distances and bond angles of interest in a series of bis-indole derivatives have been discussed in detail. The biological activity of the substances has been correlated with based the structure-activity relationships (SAR) base which provides the different possibility of activity (Pa) and possibility of inactivity (Pi). For a better understanding of the packing interactions existing among these derivatives, an overview of crystal structure analysis with emphasis on the intramolecular hydrogen bonding in some bis-indole derivatives is presented. The role of hydrogen bonding in the crystal structure assembly of bis-indole derivatives has been found to be predominant and this observation reveals significant impact of hydrogen bonding in high value of drug-likeness of these bio-molecules.


icon graph This Abstract was viewed 679 times | icon graph Article PDF downloaded 294 times

How to Cite
(1)
Sharma, V.; Brahmachari, G.; Gupta, V. K. Crystallographic Structure, Activity Prediction, and Hydrogen Bonding Analysis of Some CSD-Based 3,3’-Bis-Indole Derivatives: A Review. Eur. J. Chem. 2021, 12, 493-501.

Article Details

Share
Links for Article


Crossref - Scopus - Google - European PMC
Crossref
Scopus
Google Scholar
Europe PMC
References

[1]. Safe, S.; Papineni, S.; Chintharlapalli, S. Cancer Lett. 2008, 269 (2), 326-338.
https://doi.org/10.1016/j.canlet.2008.04.021

[2]. Chu, X.-Q.; Zi, Y.; Lu, X.-M.; Wang, S.-Y.; Ji, S.-J. Tetrahedron 2014, 70 (2), 232-238.
https://doi.org/10.1016/j.tet.2013.11.079

[3]. Wong, G. Y.; Bradlow, L.; Sepkovic, D.; Mehl, S.; Mailman, J.; Osborne, M. P. J. Cell. Biochem. Suppl. 1997, 28-29, 111-116.
https://doi.org/10.1002/(SICI)1097-4644(1997)28/29+<111::AID-JCB12>3.0.CO;2-K

[4]. Raj, M. H. G.; Abd Elmageed, Z. Y.; Zhou, J.; Gaur, R. L.; Nguyen, L.; Azam, G. A.; Braley, P.; Rao, P. N.; Fathi, I. M.; Ouhtit, A. Gynecol. Oncol. 2008, 110 (3), 432-438.
https://doi.org/10.1016/j.ygyno.2008.05.001

[5]. Bell, M. C.; Crowley-Nowick, P.; Bradlow, H. L.; Sepkovic, D. W.; Schmidt-Grimminger, D.; Howell, P.; Mayeaux, E. J.; Tucker, A.; Turbat-Herrera, E. A.; Mathis, J. M. Gynecol. Oncol. 2000, 78 (2), 123-129.
https://doi.org/10.1006/gyno.2000.5847

[6]. Garikapaty, V. P. S.; Ashok, B. T.; Tadi, K.; Mittelman, A.; Tiwari, R. K. Biochem. Biophys. Res. Commun. 2006, 340 (2), 718-725.
https://doi.org/10.1016/j.bbrc.2005.12.059

[7]. Kolonel, L. N.; Hankin, J. H.; Wilkens, L. R.; Fukunaga, F. H.; Hinds, M. W. Cancer Causes Control 1990, 1 (3), 223-234.
https://doi.org/10.1007/BF00117474

[8]. Fowke, J. H. Eur. J. Cancer Prev. 2007, 16 (4), 348-356.
https://doi.org/10.1097/01.cej.0000236258.80522.fb

[9]. Aronchik, I.; Kundu, A.; Quirit, J. G.; Firestone, G. L. Mol. Cancer Res. 2014, 12 (11), 1621-1634.
https://doi.org/10.1158/1541-7786.MCR-14-0018

[10]. Fan, S.; Meng, Q.; Xu, J.; Jiao, Y.; Zhao, L.; Zhang, X.; Sarkar, F. H.; Brown, M. L.; Dritschilo, A.; Rosen, E. M. Proc. Natl. Acad. Sci. U. S. A. 2013, 110 (46), 18650-18655.
https://doi.org/10.1073/pnas.1308206110

[11]. Sundberg, R. The Chemistry of Indoles; Academic Press: San Diego, CA, 1970.

[12]. Kayet, A.; Singh, V. K. Org. Biomol. Chem. 2017, 15 (33), 6997-7007.
https://doi.org/10.1039/C7OB01701D

[13]. Zhang, D.-M.; Tang, Q.-G.; Ji, C.-X.; Guo, C. Acta Crystallogr. Sect. E Struct. Rep. Online 2007, 63 (1), o81-o82.
https://doi.org/10.1107/S1600536806051294

[14]. Mandal, S. M.; Pegu, R.; Porto, W. F.; Franco, O. L.; Pratihar, S. Bioorg. Med. Chem. Lett. 2017, 27 (10), 2135-2138.
https://doi.org/10.1016/j.bmcl.2017.03.070

[15]. Wang, S.-Y.; Ji, S.-J. Tetrahedron 2006, 62 (7), 1527-1535.
https://doi.org/10.1016/j.tet.2005.11.011

[16]. Li, Y.-L.; Sun, H.-S.; Jiang, H.; Xu, N.; Xu, H. Acta Crystallogr. Sect. E Struct. Rep. Online 2014, 70 (10), 259-261.
https://doi.org/10.1107/S1600536814020686

[17]. Zhuo, M.-H.; Liu, G.-F.; Song, S.-L.; An, D.; Gao, J.; Zheng, L.; Zhang, S. Adv. Synth. Catal. 2016, 358 (5), 808-815.
https://doi.org/10.1002/adsc.201500985

[18]. Sharma, S.; Banerjee, B.; Brahmachari, G.; Kant, R.; Gupta, V. K. Crystallogr. Rep. 2016, 61 (2), 225-229.
https://doi.org/10.1134/S1063774516020218

[19]. Deng, X.; Wu, D.; Huang, X.; Luo, F. Acta Crystallogr. Sect. E Struct. Rep. Online 2011, 67 (7), o1603-o1603.
https://doi.org/10.1107/S1600536811020411

[20]. Kinthada, L. K.; Ghosh, S.; De, S.; Bhunia, S.; Dey, D.; Bisai, A. Org. Biomol. Chem. 2013, 11 (40), 6984-6993.
https://doi.org/10.1039/c3ob41482e

[21]. Brahmachari, G.; Banerjee, B. ACS Sustain. Chem. Eng. 2014, 2 (12), 2802-2812.
https://doi.org/10.1021/sc500575h

[22]. Zeng, X.-F.; Ji, S.-J.; Su, X.-M. Chin. J. Chem. 2008, 26 (3), 413-416.
https://doi.org/10.1002/cjoc.200890078

[23]. Krishna, R.; Velmurugan, D.; Shanmuga Sundara, S. Acta Crystallogr. C 1999, 55 (8), IUC9900084.
https://doi.org/10.1107/S0108270199099047

[24]. Yu, H.; Yu, Z. Angew. Chem. Int. Ed Engl. 2009, 48 (16), 2929-2933.
https://doi.org/10.1002/anie.200900278

[25]. Mandal, M.; Kumar, D.; Roy, R.; Sen, R.; Das, P.; Chatterjee, M.; Jaisankar, P. Bioorg. Med. Chem. Lett. 2011, 21 (10), 3084-3087.
https://doi.org/10.1016/j.bmcl.2011.03.028

[26]. Tang, S.-G.; Zhang, D.-M.; Wu, W.-Y.; Shan, L.; Guo, C. Acta Crystallogr. Sect. E Struct. Rep. Online 2006, 62 (10), o4691-o4692.
https://doi.org/10.1107/S1600536806038293

[27]. Lin, X.; Cui, S.; Wang, Y. Synth. Commun. 2006, 36 (21), 3153-3160.
https://doi.org/10.1080/00397910600908819

[28]. Kumar, R. A.; Naveen, S.; Kumar, T. O. S.; Mahadevan, K. M.; Kumara, M. N.; Lokanath, N. K. CCDC 1497585: Experimental Crystal Structure Determination, 2017.

[29]. Xu, X.-F.; Xiong, Y.; Ling, X.-G.; Xie, X.-M.; Yuan, J.; Zhang, S.-T.; Song, Z.-R. Chin. Chem. Lett. 2014, 25 (3), 406-410.
https://doi.org/10.1016/j.cclet.2013.11.038

[30]. Deb, M. L.; Deka, B.; Saikia, P. J.; Baruah, P. K. Tetrahedron Lett. 2017, 58 (20), 1999-2003.
https://doi.org/10.1016/j.tetlet.2017.04.032

[31]. Selvanayagam, S.; Chandak, M. S.; Velmurugan, D.; Ravikumar, K.; Raghunathan, R. Acta Crystallogr. Sect. E Struct. Rep. Online 2005, 61 (10), o3122-o3123.
https://doi.org/10.1107/S1600536805027248

[32]. Ganesan, M.; Gambarotta, S.; Yap, G. P. A. CCDC 140500: Experimental Crystal Structure Determination, 2000.

[33]. Sun, H.-S.; Li, Y.-L.; Jiang, H.; Xu, N.; Xu, H. Acta Crystallogr. E Crystallogr. Commun. 2015, 71 (10), 1140-1142.
https://doi.org/10.1107/S205698901501628X

[34]. Karmakar, S.; Das, P.; Ray, D.; Ghosh, S.; Chattopadhyay, S. K. Org. Lett. 2016, 18 (20), 5200-5203.
https://doi.org/10.1021/acs.orglett.6b02321

[35]. Narayanan, P.; Sethusankar, K.; Ramachandiran, K.; Perumal, P. T. Acta Crystallogr. Sect. E Struct. Rep. Online 2011, 67 (12), o3196-o3196.
https://doi.org/10.1107/S1600536811045491

[36]. Chinta, B. S.; Baire, B. Tetrahedron 2016, 72 (49), 8106-8116.
https://doi.org/10.1016/j.tet.2016.10.067

[37]. Beltrá, J.; Gimeno, M. C.; Herrera, R. P. Beilstein J. Org. Chem. 2014, 10, 2206-2214.
https://doi.org/10.3762/bjoc.10.228

[38]. Hui, Y.; Wang, C.; Shi, W.; Meng, H.; Xie, Z. Youji huaxue 2014, 34 (5), 898-902.
https://doi.org/10.6023/cjoc201311014

[39]. Ravikumar, P.; Bahuguna, A.; Sharma, R.; Sagara, P. Synlett 2016, 28 (01), 117-121.
https://doi.org/10.1055/s-0036-1588885

[40]. Guo, C.; Zhang, D.-M.; Tang, Q.-G.; Sun, H.-S. Acta Crystallogr. Sect. E Struct. Rep. Online 2006, 62 (9), o3994-o3995.
https://doi.org/10.1107/S1600536806032727

[41]. Naidu, P. S.; Majumder, S.; Bhuyan, P. J. Mol. Divers. 2015, 19 (4), 685-693.
https://doi.org/10.1007/s11030-015-9605-3

[42]. Sun, H.-S.; Li, Y.-L.; Xu, N.; Xu, H.; Zhang, J.-D. Acta Crystallogr. Sect. E Struct. Rep. Online 2013, 69 (10), o1516-o1516.
https://doi.org/10.1107/S1600536813024471

[43]. Zhang, D.-M.; Tang, S.-G.; Wu, W.-Y.; Tang, Q.-G.; Guo, C. Acta Crystallogr. Sect. E Struct. Rep. Online 2006, 62 (12), o5467-o5468.
https://doi.org/10.1107/S1600536806046393

[44]. Krishna, R.; Velmurugan, D.; Babu, G.; Perumal, P. T. Acta Crystallogr. C 1999, 55 (1), 75-78.
https://doi.org/10.1107/S0108270198010695

[45]. Ji, S.-J.; Wang, S.-Y.; Zhang, Y.; Loh, T.-P. Tetrahedron 2004, 60 (9), 2051-2055.
https://doi.org/10.1016/j.tet.2003.12.060

[46]. Griffiths, K.; Kumar, P.; Akien, G. R.; Chilton, N. F.; Abdul-Sada, A.; Tizzard, G. J.; Coles, S. J.; Kostakis, G. E. Chem. Commun. (Camb.) 2016, 52 (50), 7866-7869.
https://doi.org/10.1039/C6CC03608B

[47]. Sain, D.; Kumari, C.; Kumar, A.; Dey, S. Supramol. Chem. 2016, 28 (3-4), 239-248.
https://doi.org/10.1080/10610278.2015.1092534

[48]. Neshat, A. RSC Adv. 2016, 6 (39), 32839-32848.
https://doi.org/10.1039/C6RA01391K

[49]. Anil Kumar, R.; Naveen, S.; Shrungesh Kumar, T. O.; Mahadevan, K. M.; Kumara, M. N.; Lokanath, N. K. IUCrdata 2016, 1 (6). https://doi.org/10.1107/s2414314616008385.
https://doi.org/10.1107/S2414314616008385

[50]. Jadhav, S. D.; Bakshi, D.; Singh, A. J. Org. Chem. 2015, 80 (20), 10187-10196.
https://doi.org/10.1021/acs.joc.5b01736

[51]. Merinos, J.; Ruiz, H.; Lopez, Y.; Lima, S. Lett. Org. Chem. 2015, 12 (5), 332-336.
https://doi.org/10.2174/1570178612666150220225335

[52]. Beltrá, J.; Gimeno, M. C.; Herrera, R. P. Beilstein J. Org. Chem. 2014, 10, 2206-2214.
https://doi.org/10.3762/bjoc.10.228

[53]. Zhang, C.-L.; Ye, P.-P.; Du, Z.-Q. Acta Crystallogr. Sect. E Struct. Rep. Online 2009, 65 (6), o1332-o1332.
https://doi.org/10.1107/S1600536809017759

[54]. Poroikov, V. V.; Filimonov, D. A.; Ihlenfeldt, W.-D.; Gloriozova, T. A.; Lagunin, A. A.; Borodina, Y. V.; Stepanchikova, A. V.; Nicklaus, M. C. J. Chem. Inf. Comput. Sci. 2003, 43 (1), 228-236.
https://doi.org/10.1021/ci020048r

[55]. Marjo, C. E.; Scudder, M. L.; Craig, D. C.; Bishop, R. J. Chem. Soc., Perkin Trans. 2 1997, No. 10, 2099-2104.
https://doi.org/10.1039/a700494j

[56]. Macrae, C. F.; Bruno, I. J.; Chisholm, J. A.; Edgington, P. R.; McCabe, P.; Pidcock, E.; Rodriguez-Monge, L.; Taylor, R.; van de Streek, J.; Wood, P. A. J. Appl. Crystallogr. 2008, 41 (2), 466-470.
https://doi.org/10.1107/S0021889807067908

[57]. Steiner, T.; Desiraju, G. R. Chem. Commun. (Camb.) 1998, 8, 891-892.
https://doi.org/10.1039/a708099i

Supporting Agencies

University of Jammu, Rashtriya Uchchatar Shiksha Abhiyan (RUSA) 2.0 Project (Ref. No, RUSA/JU/2/ 2019-20/111/3588-3636), Jammu, India.
Most read articles by the same author(s)
TrendMD

Dimensions - Altmetric - scite_ - PlumX

Downloads and views

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...
License Terms

License Terms

by-nc

Copyright © 2024 by Authors. This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at https://www.eurjchem.com/index.php/eurjchem/terms and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License (http://creativecommons.org/licenses/by-nc/4.0). By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution, or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License (https://www.eurjchem.com/index.php/eurjchem/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).