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Synthesis 2023; 55(24): 4145-4162
DOI: 10.1055/a-2161-0283
DOI: 10.1055/a-2161-0283
paper
Stereoselective Synthesis of Highly Functionalized Aminobenzothiazole-Fused Spirooxindole Derivatives: in silico and in vitro Anti-Diabetic Studies
The authors SV and NN would like to thank DST-FIST-SR/FST/CS-II/2018/64 for funding the NMR Auto Sampler and HR-MS instrument facilities.
Abstract
A series of highly functionalized spirooxindole pyrrolizidine/pyrrolothiazole derivatives have been synthesized by the three-component 1,3-dipolar cycloaddition reaction of benzothiazolyl amides with isatin-based azomethine ylides. The pharmacologically significant spirooxindole derivatives bearing one quaternary carbon and four stereocenters were obtained in excellent yields (up to 93%). The compounds were screened for their anti-diabetic activity against two enzymes, α-glucosidase and α-amylase. The results exhibited potent inhibitory activity against these enzymes, especially N-(benzo[d]thiazol-2-yl)-5-fluoro-2-oxo-7′-phenyl-1′,6′,7′,7a′-tetrahydro-3′H-spiro[indoline-3,5′-pyrrolo[1,2-c]thiazole]-6′-carboxamide (6b), which showed excellent activity compared to the standard acarbose. Molecular docking against the receptors showed excellent interactions of the synthesized compounds in a similar way to acarbose. Further, the docking results of the spirooxindole pyrrolothiazole (6b) evinced the strong binding interactions of the compound with the receptors. Additionally, molecular dynamics simulations were carried out and confirmed the stability of the spirooxindole pyrrolothiazole (6b) in the active pockets of enzymes over 100 ns.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2161-0283.
- Supporting Information
Publikationsverlauf
Eingereicht: 04. Juli 2023
Angenommen nach Revision: 28. August 2023
Accepted Manuscript online:
28. August 2023
Artikel online veröffentlicht:
04. Oktober 2023
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References
- 1a Fajkusova D, Pesko M, Keltosova S, Guo J, Oktabec Z, Vejsova M, Kollar P, Coffey A, Csollei J, Kralova K, Jampilek J. Bioorg. Med. Chem. 2012; 20: 7059
- 1b Chikhale R, Menghani S, Babu R, Bansode R, Bhargavi G, Karodia N, Rajasekharan MV, Paradkar A, Khedekar P. Eur. J. Med. Chem. 2015; 96: 30
- 1c Ghosh AK, Rao KV, Nyalapatla PR, Osswald HL, Martyr CD, Aoki M, Hayashi H, Agniswamy J, Wang YF, Bulut H, Das D, Weber IT, Mitsuya H. J. Med. Chem. 2017; 60: 4267
- 2 Heusden J, Ginckel R, Bruwiere H, Moelans P, Janssen B, Floren W, Leede B, Dun J, Sanz G, Venet M, Dillen L, Hove C, Willemsens G, Janicot M, Wouters W. Br. J. Cancer 2002; 86: 605
- 3 Hockly E, Tse J, Barker A, Moolman D, Beunard J, Revington A, Holt K, Sunshine S, Moffitt H, Sathasivam K, Woodman B, Wanker E, Lowden P, Bates G. Neurobiol. Dis. 2006; 21: 228
- 4 Colombo F, Tintori C, Furlan A, Borrelli S, Christodoulou MS, Dono R, Maina F, Botta M, Amat M, Bosch J, Passarella D. Bioorg. Med. Chem. Lett. 2012; 22: 4693
- 5 Song EY, Kaur N, Park MY, Jin Y, Lee K, Kim G, Lee KY, Yang JS, Shin JH, Nam KY, No KT, Han G. Eur. J. Med. Chem. 2008; 43: 1519
- 6 Hartmann R, Frotscher M, Marchais-Oberwinkler S, Oster A, Spadaro A. PCT Int. Appl WO2012025638, 2012
- 7a Jimonet P, Audiau F, Barreau M, Blanchard JC, Boireau A, Bour Y, Coleno MA, Doble A, Doerflinger G, Huu CD, Donat MH, Duchesne JM, Ganil P, Gueremy C, Honore E, Just B, Kerphirique R, Gontier S, Hubert P, Laduron PM, Blevec JL, Meunier M, Miquet JM, Nemecek C, Pasquet M, Piot O, Pratt J, Rataud J, Reibaud M, Stutzmann JM, Mignani S. J. Med. Chem. 1999; 42: 2828
- 7b Doble A. Neurology 1996; 47: S233
- 8 Yamazaki K, Kaneko Y, Suwa K, Ebara S, Nakazawa K, Yasuno K. Bioorg. Med. Chem. 2005; 13: 2509
- 9a Zhang J, Lu X, Li T, Wang S, Zhong G. J. Org. Chem. 2017; 82: 5222
- 9b Bhoi MN, Borad MA, Patel HD. Synth. Commun. 2014; 44: 2427
- 10a Wang Y, Cobo AA, Franz AK. Org. Chem. Front. 2021; 8: 4315
- 10b Singh GS, Desta ZY. Chem. Rev. 2012; 112: 6104
- 10c Mei GJ, Shi F. Chem. Commun. 2018; 54: 6607
- 10d Cheng D, Ishihara Y, Tan B, Barbas CF. ACS Catal. 2014; 4: 743
- 10e Boddy AJ, Bull JA. Org. Chem. Front. 2021; 8: 1026
- 10f Molteni G, Silvani A. Eur. J. Org. Chem. 2021; 1653
- 11a Yu Q, Guo P, Jian J, Chen Y, Xu J. Chem. Commun. 2018; 54: 1125
- 11b Lerchner A, Carreira EM. Chem. Eur. J. 2006; 12: 8208
- 12a Yu S, Qin D, Shangary S, Chen J, Wang G, Ding K, McEachern D, Qiu S, Nikolovska-Coleska Z, Miller R, Kang S, Yang D, Wang S. J. Med. Chem. 2009; 52: 7970
- 12b Ding K, Lu Y, Nikolovska-Coleska Z, Wang G, Qiu S, Shangary S, Gao W, Qin D, Stuckey J, Krajewski K, Roller PP, Wang S. J. Med. Chem. 2006; 49: 3432
- 13 Prado EG, Gimenez MD. G, De la Puerta Vazquez R, Sanchez JL. E, Rodriguez MT. S. Phytomedicine 2007; 14: 280
- 14a Zhang X, Liu M, Zhan D, Kaur M, Jasinski JP, Zhang W. New J. Chem. 2022; 46: 3866
- 14b Zhang X, Gao Y, Liu Y, Miao Z. J. Org. Chem. 2021; 86: 8630
- 14c Yang F, Sun W, Meng H, Chen M, Chen C, Zhu B. Org. Chem. Front. 2021; 8: 283
- 14d Xiao JA, Li JL, Cheng XL, Chen K, Peng H, Chen WQ, Su W, Huang YM, Yang H. Chem. Commun. 2021; 57: 4456
- 14e Warghude PK, Sabale AS, Dixit R, Vanka K, Bhat RG. Org. Biomol. Chem. 2021; 19: 4338
- 16 Najera C, Sansano JM. Pure Appl. Chem. 2019; 91: 575
- 17a Brandao P, Marques CS, Carreiro EP, Pineiro M, Burke AJ. Chem. Rec. 2021; 21: 924
- 17b Hashimoto T, Maruoka K. Chem. Rev. 2015; 115: 5366
- 18a Saeed R, Sakla AP, Shankaraiah N. Org. Biomol. Chem. 2021; 19: 7768
- 18b Gui HZ, Wei Y, Shi M. Chem. Asian J. 2020; 15: 1225
- 18c Dondas HA, de Gracia Retamosa M, Sansano JM. Synthesis 2017; 49: 2819
- 19a Zhang M, Yang W, Li K, Sun K, Ding J, Yang L, Zhu C. Synthesis 2019; 51: 3847
- 19b Yue J, Chen S, Zuo X, Liu XL, Xu SW, Zhou Y. Tetrahedron Lett. 2019; 60: 137
- 19c Vidya S, Priya K, Velayudhan Jayasree D, Deepthi A, Biju PG. Synth. Commun. 2019; 49: 1592
- 20 Patil SM, Shirahatti PS, Ramu R. J. Pharm. Pharmacol. 2022; 74: 681
- 21 Ramu R, Patil SM. Oman Med. J. 2021; 36: e281
- 22 Rachdaoui N. Int. J. Mol. Sci. 2020; 21: 1770
- 23 Cerf ME. Front. Endocrinol. 2013; 4: 37
- 24 Ramu R, Shirahatti PS, Deepika TH, Bajpe SN, Sreepathi N, Patil SM, Prasad N. J. Appl. Biol. Biotechnol. 2022; 10: 56
- 25 Rizza RA, Vella A. Diabetes mellitus . In Pharmacology and Therapeutics: Principles to Practice . Waldman SA, Terzic A. Saunders; Philadelphia: 2009: 557-570
- 26 Date K. Regulatory Functions of α-Amylase in the Small Intestine Other than Starch Digestion: α-Glucosidase Activity, Glucose Absorption, Cell Proliferation, and Differentiation . In New Insights Into Metabolic Syndrome. Takada A. IntechOpen; London: 2020.
- 27 Cheng HM, Mah KK, Seluakumaran K. Defining Physiology: Principles, Themes, Concepts, Vol. 2. Springer; Cham (Switzerland): 2020: 59-61
- 28 Duhan M, Singh R, Devi M, Sindhu J, Kumar P, Kumar S, Kataria R, Kumar A, Lal S, Singh D. New J. Chem. 2023; 47: 5399
- 29 Toumi A, Boudriga S, Hamden K, Sobeh M, Cheurfa M, Askri M, Knorr M, Strohmann C, Brieger L. Bioorg. Chem. 2021; 106: 104507
- 30 Altowyan MS, Barakat A, Al-Majid AM, Al-Ghulikah HA. Molecules 2019; 24: 2432
- 31 Barakat A, Islam MS, Ali M, Al-Majid AM, Alshahrani S, Alamary AS, Yousuf S, Choudhary MI. Symmetry 2021; 13: 1426
- 32 Nivetha N, Martiz RM, Patil SM, Ramu R, Sreenivasa S, Velmathi S. RSC Adv. 2022; 12: 24192
- 33 Maradesha T, Patil SM, Al-Mutairi KA, Ramu R, Madhunapantula SV, Alqadi T. Molecules 2022; 27: 1888
- 34 Shivanna C, Patil SM, Mallikarjunaswamy M, Ramu R, Akhileshwari P, Nagaraju LR, Sridhar MA, Khanum SA, Ranganatha L, Silina E, Stupin V, Achar RR. Crystals 2022; 12: 960
- 35 Ramu R, Shirahatti PS, Zameer F, Ranganatha LV, Prasad MN. South Afr. J. Bot. 2014; 95: 54
- 36 Ramu R, Shirahatti PS, Deepika TH, Bajpe SN, Sreepathi N, Patil SM, Prasad N. J. Appl. Biol. Biotechnol. 2022; 10: 56
- 37 Patil SM, Martiz RM, Ramu R, Shirahatti PS, Prakash A, Kumar BP, Kumar N. J. Biomol. Struct. Dyn. 2021; 7: 1
- 38 Bompard-Gilles C, Rousseau P, Rouge P, Payan F. Structure 1996; 4: 1441
- 39 Patil SM, Maruthi KR, Bajpe NS, Vyshali VM, Sushmitha S, Chagalamari A, Ramith R. Bioinformation 2021; 7: 932
- 40 Patil SM, Martiz RM, Ramu R, Shirahatti PS, Prakash A, Chandra JS, Ranganatha LV. J. Biomol. Struct. Dyn. 2021; 11: 1
- 41 Patil SM, Martiz RM, Satish AM, Shbeer AM, Ageel M, Al-Ghorbani M, Parameswaran S, Ramu R. Molecules 2022; 27: 3888
- 42 Patil SM, Al-Mutairi KA, Firdose N, Ramu R, Martiz RM, Ashwini P. South Afr. J. Bot. 2022; 149: 712
- 43 Martiz RM, Patil SM, Ramu R, Jayanthi M, Ashwini P, Ranganatha LV, Khanum SA, Silina E, Stupin V, Achar RR. PLoS One 2022; 17: e0265022
- 44 Gurupadaswamy HD, Ranganatha VL, Ramu R, Patil SM, Khanum SA. J. Iran. Chem. Soc. 2022; 1: 1
- 45 Ganavi D, Ramu R, Kumar V, Patil SM, Martiz RM, Shirahatti PS, Sathyanarayana R, Poojary B, Holla BS, Poojary V. Arch. Pharm. (Weinheim) 2021; 12: e2100342
- 46 Martiz RM, Patil SM, Abdulaziz M, Babalghith A, Al-Areefi M, Al-Ghorbani M, Kumar JM, Prasad A, Nagalingaswamy NP. M, Ramu R. Molecules 2022; 27: 2398
- 47 Kumar V, Shetty P, Arunodaya HS, Chandra KS, Ramu R, Patil SM, Baliga A, Rai VM, Shenoy MS, Udupi V, Poojary V, Poojary B. Chem. Biodiversity 2022; 19: e202100532
- 48 Kumar V, Ramu R, Shirahatti PS, Kumari VC, Sushma P, Mandal SP, Patil SM. ChemSelect 2021; 6: 9637
- 49 Sajal H, Patil SM, Raj R, Shbeer AM, Ageel M, Ramu R. Molecules 2022; 27: 5133
- 50 Jyothi M, Khamees HA, Patil SM, Ramu R, Khanum SA. J. Iran. Chem. Soc. 2022; 10: 1