118
Views
1
CrossRef citations to date
0
Altmetric
Research Articles

Regio- and Stereoselective Synthesis of Dispiropyrrolidineoxindole Derivatives by Using Classical and Microwave Conditions, and Molecular Docking Studies of Them as Potential Cyclin Dependent Kinases (CDK5) Inhibitors

, , , &
Pages 6898-6910 | Received 19 Apr 2022, Accepted 17 Sep 2022, Published online: 30 Sep 2022

References

  • (a) S. M. Gomha, and S. M. Riyadh, “Multicomponent Synthesis of Novel Penta-Heterocyclic Ring Systems Incorporating a Benzopyranopyridine Scaffold,” Synthesis 46, no. 02 (2013): 258–62; (b) S. Abu-Melha, Z. A. Muhammad, A. S. Abouzid, M. M. Edrees, A. S. A. Dena, S. Nabil, and S. M. Gomha, “Multicomponent Synthesis, DFT Calculations and Molecular Docking Studies of Novel Thiazolyl-Pyridazinones as Potential Antimicrobial Agents against Antibiotic-Resistant Bacteria,” Journal of Molecular Structure 1234 (2021): 130180; (c) S. M. Gomha, N. A. Kheder, A. O. Abdelhamid, and Y. N. Mabkhot, “One Pot Single Step Synthesis and Biological Evaluation of Some Novel Bis(1,3,4-Thiadiazole) Derivatives as Potential Cytotoxic Agents,” Molecules 21, no. 11 (2016): 1532; (d) K. Bahrami, M. M. Khodaei, N. Batooie, N. Hosseinzadeh, and A. Foroumadi, “Hexyltriphenylphosphonium Bromide as an Absolutely Chemoselective Ionic Liquid Catalyst in the Three‐Component Reaction of Aryl Aldehydes, Acetophenones and Malononitrile,” ChemistrySelect 4, no. 20 (2019): 6190–3; (e) Gomha, S. M. Muhammad, Z. A. Abdel, ‐Aziz, M. R. Abdel, ‐Aziz, H. M. Gaber, H. M. Elaasser, and M. M. “One-Pot Synthesis of New Thiadiazolyl-Pyridines as Anticancer and Antioxidant Agents,” Journal of Heterocyclic Chemistry 55, no. 2 (2018): 530–6. (f) G. Bahrami, N. Batooie, S. R. Mousavi, S. S. Miraghaee, N. Hosseinzadeh, S. Mousavian, A. Hoshyari, S. Sajadimajd, B. Mohammadi, and R. Hatami, “Michael-Addition-Initiated Chemoselective Three-Component Reaction for the Synthesis of 2-(3-Oxo-1,3-Diarylpropyl)Malononitrile Derivatives Using Cerium(IV) Ammonium Nitrate in Phosphorus Ionic Liquid,” Polycyclic Aromatic Compounds (2021) doi:10.1080/10406638.2021.1981407; (g) A. Rahmati, A. Moazzam, and Z. Khalesi, “A One-Pot Four-Component Synthesis of N-Arylidene-2-Aryl-Imidazo[1,2-a]Azin-3-Amines,” Tetrahedron Letters 55, no. 29 (2014): 3840–3.
  • (a) H. M. T. Albuquerque, D. C. G. A. Pinto, and A. M. S. Silva, “Microwave Irradiation: Alternative Heating Process for the Synthesis of Biologically Applicable Chromones, Quinolones, and Their Precursors,” Molecules 26, no. 20 (2021): 6293; (b) S. M. Gomha, M. M. Edrees, R. A. M. Faty, Z. A. Muhammad, and Y. N. Mabkhot, “Microwave-Assisted One Pot Three-Component Synthesis of Some Novel Pyrazole Scaffolds as Potent Anticancer Agents,” Chemistry Central Journal 11, no. 1 (2017): 37; (c) S. Abu-Melha, S. Gomha, A. Abouzied, M. Edrees, A. Abo Dena, and Z. Muhammad, “Microwave-Assisted One Pot Three-Component Synthesis of Novel Bioactive Thiazolyl-Pyridazinediones as Potential Antimicrobial Agents against Antibiotic-Resistant Bacteria,” Molecules 26, no. 14 (2021): 4260; (d) E. M. Abbas, S. M. Gomha and T. A. Farghaly, “Multicomponent Reactions for Synthesis of Bioactive Polyheterocyclic Ring Systems under Controlled Microwave Irradiation,” Arabian Journal of Chemistry 7, no. 5 (2014): 623–9; (e) N. Hosseinzadeh, M. Hasani, A. Foroumadi, H. Nadri, S. Emami, N. Samadi, M. A. Faramarzi, P. Saniee, F. Siavoshi, N. Abadian, et al, “5-Nitro-Heteroarylidene Analogs of 2-Thiazolylimino-4-Thiazolidinones as a Novel Series of Antibacterial Agents,” Medicinal Chemistry Research 22, no. 5 (2013): 2293–302.
  • A. Loupy, Microwaves in Organic Synthesis, 2nd ed. (Weinheim, Germany: WileyVCH, 2006).
  • V. G. Gude, Microwave-Mediated Biofuel Production (Boca Raton: CRC Press, 2017), 38.
  • E. Vazquez, F. Giacalone, and M. Prato, “Non-Conventional Methods and Media for the Activation and Manipulation of Carbon Nanoforms,” Chemical Society Reviews 43, no. 1 (2014): 58–69.
  • (a) J. Safaei-Ghomi and R. Masoomi, “Rapid Microwave-Assisted Synthesis of N-Benzyl Fulleropyrrolidines under Solvent Free Conditions,” RSC Advances 5, no. 20 (2015): 15591–6; (b) Loupy, André, and Antonio de la Hoz, eds. Microwaves in organic synthesis. John Wiley & Sons, 2013.‏.; (c) B. Jin, R.-F. Peng, W.-N. Yang, K. Wang, B.-Q. Yuan, and S.-J. Chu, “Solvent-Free Synthesis of N -Arylfulleropyrrolidine Derivatives without Using Phase-Transfer Catalyst under Microwave Irradiation,” Synthetic Communications 40, no. 4 (2010): 580–6.
  • (a) M. Singh, A. V. Amrutha Krishnan, R. Mandal, J. Samanta, V. Ravichandiran, R. Natarajan, Y. P. Bharitkar, and A. Hazra, “Azomethine Ylide Cycloaddition: A Versatile Tool for Preparing Novel Pyrrolizidino-Spiro-Oxindolo Hybrids of the Doubly Conjugated Alkamide Piperine,” Molecular Diversity 24, no. 3 (2020): 627–39; (b) M. Anusha Rani, S. Vivek Kumar, K. Malathi, M. Muthu, A. I. Almansour, R. Suresh Kumar, and R. Ranjith Kumar, “A One-Pot Multicomponent 1,3-Dipolar Cycloaddition Strategy: Combinatorial Synthesis of Dihydrothiophenone-Engrafted Dispiro Hybrid Heterocycles,” ACS Combinatorial Science 19, no. 5 (2017): 308–14; (c) S. Bhandari, S. Sana, B. Sridhar, and N. Shankaraiah, “Microwave‐Assisted One‐Pot [3 + 2] Cycloaddition of Azomethine Ylides and 3‐Alkenyl Oxindoles: A Facile Approach to Pyrrolidine‐Fused Bis‐Spirooxindoles,” ChemistrySelect 4, no. 5 (2019): 1727–30.
  • M. G. Kulkarni, A. P. Dhondge, S. W. Chavhan, A. S. Borhade, Y. B. Shaikh, D. R. Birhade, M. P. Desai, and N. R. Dhatrak, " Total synthesis of (±)-coerulescine and (±)-horsfiline,"Beilstein Journal of Organic Chemistry 6 (2010): 876–9.
  • I. Chogii, and J. T. Njardarson, “Asymmetric [3 + 2] Annulation Approach to 3-Pyrrolines: Concise Total Syntheses of (−)-Supinidine, (−)-Isoretronecanol, and (+)-Elacomine,” Angewandte Chemie 127, no. 46 (2015): 13910–4.
  • Z. Zhang, W. Zhang, F. Kang, F. C. F. Ip, N. Y. Ip, and R. Tong, “Asymmetric Total Syntheses of Rhynchophylline and Isorhynchophylline,” The Journal of Organic Chemistry 84, no. 17 (2019): 11359–65.
  • X. Tian, Y. Zhang, W. Ren, and Y. Wang, “Synthesis of Functionalized 3,2′-Pyrrolidinyl Spirooxindoles via Domino 1,6-Addition/Annulation Reactions of Para -Quinone Methides and 3-Chlorooxindoles,” Organic Chemistry Frontiers 9, no. 3 (2022): 615–26.
  • T. H. Li and D. M. Du, “Asymmetric Synthesis of Isoxazole and Trifluoromethyl-Containing 3,2'-Pyrrolidinyl Dispirooxindoles via Squaramide-Catalysed [3 + 2] Cycloaddition Reactions,” Organic & Biomolecular Chemistry 20, no. 4 (2022): 817–23.
  • M. S. Islam, M. Haukka, S. M. Soliman, A. M. Al-Majid, A. F. M. Motiur Rahman, A. Bari, and A. Barakat, “Regio- and Stereoselective Synthesis of Spiro-Heterocycles Bearing the Pyrazole Scaffold via [3 + 2] Cycloaddition Reaction,” Journal of Molecular Structure 1250 (2022): 131711.
  • C. Yang, Y. Fang, X. Luo, D. Teng, Zh Liu, Y. Zhou, and G. Liao, “Discovery of Natural Product-like Spirooxindole Derivatives as Highly Potent and Selective LSD1/KDM1A Inhibitors for AML Treatment,” Bioorganic Chemistry 120 (2022): 105596.
  • S. Askri, m Dbeibia, C. Mchiri, S. Boudriga, M. Knorr, E. Roulland, l Laprévote, N. S. Merceron, and R. Gharbi, “Antimicrobial Activity and in Silico Molecular Docking Studies of Pentacyclic Spiro[Oxindole-2,3′-Pyrrolidines] Tethered with Succinimide Scaffolds,” Applied Sciences 12, no. 1 (2021): 360.
  • X. Zhang, M. Liu, D. Zhan, M. Kaur, J. P. Jasinski, and W. Zhang, “Three-Component [3 + 2] Cycloaddition for Regio- and Diastereoselective Synthesis of Spirooxindole-Pyrrolidines,” New Journal of Chemistry 46, no. 8 (2022): 3866–70.
  • A. Shikari, K. Mandal, D. Chopra, and S. C. Pan, “Organocatalytic Asymmetric Synthesis of Cyclic Acetals with Spirooxindole Skeleton,” Advanced Synthesis & Catalysis 364, no. 1 (2022): 58–63.
  • S. Kathiravan, D. Vijayarajan, and R. Raghunathan, “Novel Synthesis of Naphtho[2,1-b]Pyrano Pyrrolizidines and Indolizidines through Intramolecular 1,3-Dipolar Cycloaddition Reaction,” Tetrahedron Letters. 51, no. 23 (2010): 3065–70.
  • M. Zhang, W. Yang, K. Li, Ke. Sun, J. Ding, L. Yang, and Ch Zhu, "Facile Synthesis of Dispiroheterocycles through One-Pot [3+2] Cycloaddition, and Their Antiviral Activity," Synthesis 51, no. 20 (2019): 3847–58.
  • M. Mapelli, L. Massimiliano, C. Crovace, M. A. Seeliger, L.-H. Tsai, L. Meijer, and A. Musacchio, “Mechanism of CDK5/p25 Binding by CDK Inhibitors,” Journal of Medicinal Chemistry 48, no. 3 (2005): 671–9.
  • M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, G. A. Petersson, H. Nakatsuji, et al., Gaussian 09, Revision A.02 (Wallingford, CT: Gaussian, Inc., 2016).
  • O. Trott and A. J. Olson, “AutoDock Vina: improving the Speed and Accuracy of Docking with a New Scoring Function, Efficient Optimization, and Multithreading,” Journal of Computational Chemistry 31, no. 2 (2010): 455–61.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.