Design, Synthesis, and Screening of Pyridothieno[3,2-b]indole and Pyridothieno[3,2-c]cinnoline Derivatives as Potential Biologically Active Molecules

Vladimir K. Vasilin; Eugeniya A. Kanishcheva; Tatyana A. Stroganova; Irina G. Dmitrieva; Viktor V. Taranenko; Roman S. Tumskiy; Anastasiia V. Tumskaia; Nikolay A. Aksenov; Gennady D. Krapivin

doi:10.1055/a-1785-7191

Synthesis, Table of Contents

Synthesis 2022; 54(14): 3249-3261
DOI: 10.1055/a-1785-7191

paper

Design, Synthesis, and Screening of Pyridothieno[3,2-b]indole and Pyridothieno[3,2-c]cinnoline Derivatives as Potential Biologically Active Molecules

Authors

Vladimir K. Vasilin

^aDepartment of Bioorganic Chemistry and Technical Microbiology, Kuban State Technological University, 2, Moskovskaya st, Krasnodar 350072, Russian Federation
Eugeniya A. Kanishcheva

^bResearch Institute of Heterocyclic Compounds Chemistry, Kuban State Technological University, 2, Moskovskaya st, Krasnodar 350072, Russian Federation
Tatyana A. Stroganova∗

^aDepartment of Bioorganic Chemistry and Technical Microbiology, Kuban State Technological University, 2, Moskovskaya st, Krasnodar 350072, Russian Federation
Irina G. Dmitrieva

^cFSBSI All-Russian Research Institute of Biological Plant Protection, Krasnodar-39, 350039, Russian Federation
Viktor V. Taranenko

^dDepartment of Organic Chemistry, Kuban State Agrarian University, Kalinina st. 13, Krasnodar 350044, Russian Federation
Roman S. Tumskiy

^eInstitute of Biochemistry and Physiology of Plants and Microorganisms (IBPPM RAS), Russian Academy of Sciences, 13 Prospekt Entuziastov, Saratov 410049, Russian Federation
Anastasiia V. Tumskaia

^fChemistry Institute, Saratov State University, 83 Astrakhanskaya st., Saratov 410012, Russian Federation
Nikolay A. Aksenov

^gDepartment of Organic Chemistry, North Caucasus Federal University, Pushkina st., 1, Stavropol 355009, Russian Federation
Gennady D. Krapivin

^bResearch Institute of Heterocyclic Compounds Chemistry, Kuban State Technological University, 2, Moskovskaya st, Krasnodar 350072, Russian Federation

Abstract

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Abstract

New pyridothieno[3,2-b]indole and pyridothieno[3,2-c]cinnoline derivatives are designed and prepared from the corresponding 3-amino-2-arylthieno[2,3-b]pyridines. By a molecular docking method novel potential inhibitors of DNA gyrase B are identified among the thieno[2,3-b]pyridine derivatives. In addition, some of the prepared pyridothienoindoles exhibit in vivo antidote activity against the herbicide 2,4-D.

Key words

pyridothienoindoles - azide - thermolysis - antidote activity - DNA gyrase inhibitors - molecular docking - ADMET

Full Text

References

References

1a Mastelić A, Čikeš Čulić V, Režić Mužinić N, Vuica-Ross M, Barker D, Leung EY, Reynisson J, Markotić A. Drug Design, Development and Therapy 2017; 11: 759
1b Marijan S, Markotić A, Mastelić A, Režić-Mužinić N, Pilkington LI, Reynisson J, Čikeš Čulić V. Scientific Reports 2020; 10: 11876
1c Lauria A, Abbate I, Patella C, Martorana A, Dattolo G, Almerico AM. Eur. J. Med. Chem. 2013; 62: 416
1d Reynisson J, Jaiswal JK, Barker D, D’mello SA. N, Denny WA, Baguley BC, Leung EY. Cancer Cell Int. 2016; 16: 18
1e Eurtivong C, Semenov V, Semenova M, Konyushkin L, Atamanenko O, Reynisson J, Kiselyov A. Bioorg. Med. Chem. 2017; 25: 658
1f Zeng XX, Zheng RL, Zhou T, He HY, Liu JY, Zheng Y, Tong AP, Xiang ML, Song XR, Yang SY, Wei YQ, Zhao YL, Yang L. Bioorg. Med. Chem. Lett. 2010; 20: 6282
1g Reynisson J, Jaiswal JK, Barker D, D’mello SA. N, Denny WA, Baguley BC, Leung EY. Cancer Cell Int. 2016; 16: 18

2a Mohareb RM, Ibrahim RA. Med. Chem. Res. 2017; 26: 587
2b Leung E, Pilkington LI, van Rensburg M, Jeon CY, Song M, Arabshahi HJ, De Zoysa GH, Sarojini V, Denny WA, Reynisson J, Barker D. Bioorg. Med. Chem. 2016; 24: 1142

3a Haverkate NA, van Rensburg M, Kumara S, Reynisson J, Leung E, Pilkington LI, Barker D. Bioorg. Med. Chem. 2021; 371: 116092
3b Zafar A, Pilkington LI, Haverkate NA, Van Rensburg M, Leung E, Kumara S, Denny WA, Barker D, Alsuraifi A, Hoskins C, Reynisson J. Molecules 2018; 23: 145
3c van Rensburg M, Leung E, Haverkate NA, Eurtivong C, Pilkington LI, Reynisson J, Barker D. Bioorg. Med. Chem. Lett. 2017; 27: 135

4 Kumar GS, Poornachandra Y, Reddy KR, Kumar CG, Narsaiah B. Synth. Commun. 2017; 47: 1864
5 Liu H, Li Y, Wang X.-Y, Wang B, He H.-Y, Liu J.-Y, Xiang M.-L, He J, Wu X.-H, Yang L. Bioorg. Med. Chem. Lett. 2013; 23: 2349
6 Saito K, Shinozuka T, Nakao A, Kiho T, Kunikata T, Shiiki T, Nagai Y, Naito S. Bioorg. Med. Chem. Lett. 2019; 29: 1769
7 Pevet I, Brule C, Tizot A, Gohier A, Cruzalegui F, Boutin JA, Goldstein S. Bioorg. Med. Chem. 2011; 19: 2517
8 Zuo W.-Q, Wang N.-Y, Zhu Y.-x, Liu L, Xiao K.-J, Zhang L.-D, Gao C, Liu Z.-H, You X.-Y, Shi Y.-J, Peng C.-T, Ran K, Tang H, Yu L.-T. RSC Adv. 2016; 6: 40277

9a Sirakanyan SN, Spinelli D, Geronikaki A, Hakobyan EK, Hovakimyan AA. Synth. Commun. 2019; 49: 2823
9b Sirakanyan SN, Kartsev VG, Hakobyan EK, Hovakimyan AA. Russ. J. Org. Chem. 2018; 54: 923
9c Paronikyan EG, Dashyan SS, Minasyan NS, Stepanyan GM. Russ. J. Org. Chem. 2016; 52: 576

10a Irgashev RA, Steparuk AS, Rusinov GL. Tetrahedron 2020; 76: 131723
10b Al-Waleedy SA. H, Bakhite EA, Abbady MS, Abdu-Allah HH. M. J. Heterocycl. Chem. 2020; 57: 2379
10c Hassan AY, Sarg MT, El-Sebaey SA. J. Heterocycl. Chem. 2020; 57: 694
10d Hassan AY, Sarg MT, El-Sebaey SA. J. Heterocycl. Chem. 2019; 56: 3102
10e Sanad SM. H, Ahmed AA. M, Mekky AE. M. J. Heterocycl. Chem. 2020; 57: 590
10f Sanad SM. H, Hawass MA. E, Ahmed AA. M, Elneairy MA. A. J. Heterocycl. Chem. 2018; 55: 2823
10g Stroganova TA, Vasilin VK, Zelenskaya EA, Red’kin VM, Krapivin GD. Synthesis 2008; 3088
10h Stroganova TA, Vasilin VK, Krapivin GD. Synlett 2016; 27: 1569
10i Vasilin VK, Lukina DY, Stroganova TA, Krapivin GD, Morozov PG. Chem. Heterocycl. Compd. (Engl. Transl.) 2015; 50: 1756
10j Dotsenko VV, Lukina DY, Buryi DS, Strelkov VD, Aksenov NA, Aksenova IV. Russ. J. Gen. Chem. 2021; 91: 1292

11 Chaouni W, Aadil M, Djellal A, Kirsch G. Z. Naturforsch. B 2014; 69: 509
12 Lauria A, Abbate I, Patella C, Martorana A, Dattolo G, Almerico AM. Eur. J. Med. Chem. 2013; 62: 416

13a Organic Azides: Syntheses and Applications. Bräse S, Banert K. John Wiley and Sons, Ltd; West Sussex: 2001
13b Ren Y.-w, Wang X, Wang W, Li B, Shi Z.-J, Zhang W. Tetrahedron Lett. 2011; 52: 192
13c Parisien-Collette S, Cruché C, Abel-Snape X, Collins SK. Green Chem. 2017; 19: 4798
13d Ni H, Zhang G, Yu Y. Curr. Org. Chem. 2015; 19: 776
13e Pumphrey AL, Dong H, Driver TG. Angew. Chem. Int. Ed. 2012; 51: 5920

14a Timári G, Soós T, Hajós G. Synlett 1997; 1067
14b Tapolcsányi P, Krajsovszky G, Andó R, Lipcsey P, Horváth G, Mátyus P, Riedl Z, Hajós G, Maes BU. W, Lemière GL. F. Tetrahedron 2002; 58: 10137
14c Stockmann V, Bakke JM, Bruheim P, Fiksdahl A. Tetrahedron 2009; 65: 3668
14d Dang HV, Knobloch B, Habib NS, Kappe T, Stadlbauer W. J. Heterocycl. Chem. 2005; 42: 85

15 Kanishcheva EA, Vasilin VK, Stroganova TA, Krapivin GD. Chem. Heterocycl. Compd. (Engl. Transl.) 2013; 49: 1387

16a Vasilin VK, Kanishcheva EA, Stroganova T. А, Krapivin GD. Synlett 2015; 26: 755
16b Vasilin VK, Kanishcheva EA, Stroganova T. А, Volynkin VA, Gizhinskaya AV, Vassiliev PM, Krapivin GD. Chem. Heterocycl. Compd. (Engl. Transl.) 2020; 56: 1078

17 Kanishcheva EA, Vasilin VK, Kasimova DR, Stroganova T. А, Krapivin GD. Chem. Heterocycl. Compd. (Engl. Transl.) 2013; 48: 1883
18 Al-Trawneh SA, El-Abadelah MM, Zahra JA, Al-Taweel SA, Zani F, Incerti M, Cavazzoni A, Vicini P. Bioorg. Med. Chem. 2011; 19: 2541
19 Al-Trawneh SA, Zahra JA, Kamal MR, El-Abadelah MM, Zani F, Incerti M, Cavazzoni A, Alfieri RR, Petronini PG, Vicini P. Bioorg. Med. Chem. 2010; 18: 5873
20 Muth CW, Abraham N, Linfield ML, Wotring RB, Pacofsky EA. J. Org. Chem. 1960; 25: 736

21a Slevin A, Koolmeister T, Scobie M. Chem. Commun. 2007; 2506
21b Corbett JF, Holt PF. J. Chem. Soc. 1961; 5029
21c Barton JW, Thomas JF. J. Chem. Soc. 1964; 1265
21d Preston PN, Tennant G. Chem. Rev. 1972; 72: 627

22 Scobie M, Tennant G. J. Chem. Soc., Chem. Commun. 1993; 1756

23a Sauer J, Engels J. Tetrahedron Lett. 1969; 10: 5175
23b Smith PA. S, Boyer JH. J. Am. Chem. Soc. 1951; 73: 2626

24 CCDC 2131097 (6i) contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/structures
25 Reuter H. Acta Crystallogr., Sect. E: Crystallogr. Commun. 2017; 73: 1405
26 ChemAxon Marvin Suite ver. 21.10.0 (accessed April 4, 2022): http://www.chemaxon.com
27 Casewit CJ, Colwell KS, Rappe AK. J. Am. Chem. Soc. 1992; 114: 10035
28 Hanwell MD, Curtis DE, Lonie DC, Vandermeersch T, Zurek E, Hutchison GR. J. Cheminform. 2012; 4: 1
29 O’Boyle NM, Banck M, James CA, Morley C, Vandermeersch T, Hutchison GR. J. Cheminform. 2011; 3: 33
30 Brvar M, Perdih A, Renko M, Anderluh G, Turk D, Solmajer T. J. Med. Chem. 2012; 55: 6413
31 Cole JC, Nissink JW. M, Taylor R. Protein–ligand docking and virtual screening with GOLD . In Virtual screening in drug discovery . Taylor & Francis/CRC Press; Boca Raton: 2005
32 Pettersen EF, Goddard TD, Huang CC, Couch GS, Greenblatt DM, Meng EC, Ferrin TE. J. Comput. Chem. 2004; 25: 1605
33 Stierand K, Maaß P, Rarey M. Bioinformatics 2006; 22: 1710
34 Molinspiration Cheminformatics free web services, Slovensky Grob, Slovakia (accessed April 4, 2022): https://www.molinspiration.com
35 Pires DE, Blundell TL, Ascher DB. J. Med. Chem. 2015; 58: 4066
36 Mayer C, Janin YL. Chem. Rev. 2014; 114: 2313
37 Jain SC, Pandey MK, Upadhyay RK, Kumar R, Hundal G, Hundal MS. Phytochemistry 2006; 67: 1005
38 Lipinski CA. J. Pharmacol. Toxicol. Methods 2000; 44: 235
39 Veber DF, Johnson SR, Cheng H.-Y, Smith BR, Ward KW, Kopple KD. J. Med. Chem. 2002; 45: 2615
40 Stroganova TA, Vasilin VK, Krapivin GD, Strelkov VD, Dyadyuchenko LV. Chem. Heterocycl. Compd. (Engl. Transl.) 2016; 52: 45

41a Dmitrieva IG, Dyadyuchenko LV, Strelkov VD, Isakova LI, Krapivin GD, Zaplishniy VN. RU Patent 2276845, 2006
41b Strelkov VD, Dyadyuchenko LV, Isakova LI, Kvasenkov OI. RU Patent 2277333, 2006
41c Dmitrieva IG, Dyadyuchenko LV, Strelkov VD, Isakova LI, Tkach LN, Nazarenko DYu, Chubenko TI, Tsitovich IO. RU Patent 2475490, 2013
41d Kaigorodova EA, Vasilin VK, Tymorin VA, Nenko NI, Krapivin GD, Dyadyuchenko LV, Isakova LI, Strelkov VD. RU Patent 2232762, 2004

42 Strelkov VD, Dyadyuchenko LV, Isakova LI, Dmitrieva IG. Agrokhimiya 2010; 28
43 Dolomanov OV, Bourhis LJ, Gildea RJ, Howard JA.K, Puschmann H. J. Appl. Crystallogr. 2009; 42: 339
44 Sheldrick GM. Acta Crystallogr., Sect. A 2015; 71: 3

Supplementary Material

Supporting Information (PDF)