European Journal of Chemistry

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

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Varun Sharma
Goutam Brahmachari
Vivek Kumar Gupta

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.


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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.

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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

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