ISSN

0974-4150 (Online)
0974-4169 (Print)


Author(s): Shreyash D. Kadam, Denni Mammen, Deepak S. Kadam, Sudhakar G. Patil

Email(s): kadamshreyash28@gmail.com

DOI: 10.52711/0974-4150.2023.00010   

Address: Shreyash D. Kadam1*, Denni Mammen1, Deepak S. Kadam2, Sudhakar G. Patil2
1School of Science, Navrachana University, Vasna-Bhayli Main Rd, Bhayli, Vadodara-391410, Gujarat, India
2Organic Chemistry Research Laboratory, Maharashtra Udaygiri Mahavidyalay, Udgir-413517, Maharashtra, India
*Corresponding Author

Published In:   Volume - 16,      Issue - 1,     Year - 2023


ABSTRACT:
Thiazolidin-4-one derivatives have been hailed as “wonder nucleus” due to their profound biological activities. A number of derivatives with variable functional groups attached to the five-membered heterocyclic ring which have been synthesized and further subjected to molecular docking studies, against C-KIT Tyrosine kinase target protein (1T46). The interactions, binding and affinity variations due to differences in functional groups have been studied using ChemDraw Ultra 7.0, RCSB – Protein Data Bank, BIOVIA Discovery Studio Visualizer 2021, MGL AutoDock Tools, AutoDock Vina and Vina Split software. The docking studies showed good interaction of the synthesized molecules with the 1T46 target protein. The ADME studies of these molecules have also been studied to identify which of the synthesized molecules have the potential to cross the Human Intestinal lining (HIA), as well as the BBB barrier. Out of the 18 molecules studied, 12 of them showed good potential to be absorbed by the intestine out of which only one molecule was able to show potential to cross the BBB barrier. There were 4 molecules that could not cross both the barrier. These studies could reveal which functionalities present attached to the thiazolidin-4-one could assist in human intestinal absorption and the crossing of the BBB barrier.


Cite this article:
Shreyash D. Kadam, Denni Mammen, Deepak S. Kadam, Sudhakar G. Patil. In silico molecular docking against C-KIT Tyrosine Kinase and ADME studies of 3-Ethyl-2-(2,3,4-trifluoro-phenylimino)-thiazolidin-4-one derivatives. Asian Journal of Research in Chemistry. 2023; 16(1):55-4. doi: 10.52711/0974-4150.2023.00010

Cite(Electronic):
Shreyash D. Kadam, Denni Mammen, Deepak S. Kadam, Sudhakar G. Patil. In silico molecular docking against C-KIT Tyrosine Kinase and ADME studies of 3-Ethyl-2-(2,3,4-trifluoro-phenylimino)-thiazolidin-4-one derivatives. Asian Journal of Research in Chemistry. 2023; 16(1):55-4. doi: 10.52711/0974-4150.2023.00010   Available on: https://www.ajrconline.org/AbstractView.aspx?PID=2023-16-1-10


REFERENCES:
1.    Lengauer T, Rarey M. Computational methods for biomolecular docking. Current Opinion in Structural Biology. 1996; 6(3):402-406. doi:10.1016/s0959-440x(96)80061-3
2.    Taylor RD, Jewsbury P, Essex J. A review of protein-small molecule docking methods. J Comput Aided Mol Des. 2002; 16:155-166. doi:10.1023/A:1020155510718
3.    Attique S, Hassan M, Usman M, et al. A Molecular Docking Approach to Evaluate the Pharmacological Properties of Natural and Synthetic Treatment Candidates for Use against Hypertension. International Journal of Environmental Research and Public Health. 2019; 16(6):923. doi:10.3390/ijerph16060923
4.    María J, Yunta. Docking and Ligand Binding Affinity: Uses and Pitfalls. American Journal of Modeling and Optimization. 2016; 4(3):74-114. doi:10.12691/ajmo-4-3-2
5.    Pantsar T, Poso A. Binding Affinity via Docking: Fact and Fiction. Molecules. 2018; 23(8):1899. doi:10.3390/molecules23081899
6.    Meng XY, Zhang HX, Mezei M, Cui M. Molecular Docking: A Powerful Approach for Structure-Based Drug Discovery. Current Computer Aided-Drug Design. 2011; 7(2):146-157. doi:10.2174/157340911795677602
7.    Kumar R, Patil S. Biological prospective of 4-thiazolidinone: a review. Hygeia journal for drugs and medicines. 2017; 9(1). doi:10.15254/h.j.d.med.9.2017.166
8.    Krishna PN, Mohite YM. Insilico Activity Prediction of Thiazolidinediones Derivatives. Asian Journal of Pharmaceutical Analysis. 2018; 8(1):39. doi:10.5958/2231-5675.2018.00007.8
9.    Abhinit M, Ghodke M, Pratima NA. Exploring Potential of 4-Thiazolidinone. ChemInform. 2009; 41(35):47-64. doi:10.1002/chin.201035248
10.    Tripathi AC, Gupta SJ, Fatima GN, Sonar PK, Verma A, Saraf SK. 4-Thiazolidinones: The advances continue…. European Journal of Medicinal Chemistry. 2014; 72:52-77. doi:10.1016/j.ejmech.2013.11.017
11.    Diurno MV, Izzo AA, Mazzoni O, Bolognese A, Capasso F. Antidiarrhoeal Activity of New Thiazolidinones Related to Loperamide. Journal of Pharmacy and Pharmacology. 1996; 48(7):760-762. doi:10.1111/j.2042-7158.1996.tb03966.x
12.    Chavan AA, Pai NR. Synthesis and antimicrobial screening of 5-arylidene-2-imino-4-thiazolidinones. Arkivoc. 2007; (16):148-155. doi:10.3998/ark.5550190.0008.g16
13.    Kumar K, Singh BK. Synthesis, characterization and anti-microbial activity of some 4-thiazolidinone conjugatives. Asian Journal of Pharmaceutical Analysis. 2020; 10(4):195-200. doi:10.5958/2231-5675.2020.00036.8
14.    Gupta YK, Agarwal SC. Synthesis and antimicrobial activity of new 4-thiazolidinone derivatives containing 2-amino-6-ethoxybenzothiazole. Asian Journal of Research in Chemistry. 2011; 4(12).
15.    Preethi P, Sree K, Kumar K, Rajavelu R, Sivakumar T. Synthesis, Characterization and Its Biological Evaluation of Some Novel 4-Thiazolidinone and 2-Azetidinone Derivatives. Asian Journal of Pharmaceutical Research. 2012; 2(2):63-70.
16.    Muthumani P, Meera R, Chidambaranathan N, Devi P, Bkameswari. Synthesis and Biological Screening of Some Novel 4-Thiazolidinone Derivatives. Asian Journal of Research in Chemistry. 2009; 2(4).
17.    Srinivas Rao T, Vikram B, Akamma H. Synthesis and In Vitro Antibacterial Activity Studies of Some Substituted Aryloxy-4-Thiazolidinones. Asian Journal of Research in Chemistry. 2009; 2(3).
18.    Patel V, Patel R, Patel N, Panchal S, Bhardia P. Synthesis and Study of Some New 2-Imino-3-[Carboxamido o-hydroxyphenyl]-5-Arylidene-4-Thiazolidinone as Antibacterial Agents. Asian Journal of Research in Chemistry. 2010; 3(2).
19.    Gupta Y, Gupta V, Singh S. Synthesis, Characterization and Antibacterial Activity of Some 4-Thiazolidinones Derivatives. Asian Journal of Research in Chemistry. 2012; 5(9).
20.    Abeed A, Youssef M, Hegazy R. Synthesis, Anti-Diabetic and Renoprotective Activity of Some New Benzazole, Thiazolidin-4-one and Azetidin-2-one Derivatives. Journal of the Brazilian Chemical Society. 2017; 11(28). doi:10.21577/0103-5053.20170050
21.    Agrawal N, Upadhyay PK, Shah K, Mishra P. Antidiabetic activity of some synthesized 2-(substituted phenyl)-3-(naphthalen-1-yl) thiazolidin-4-ones. Journal of The Indian Chemical Society. 2017; 94(8):913-919.
22.    Diurno MV, Mazzoni O, Piscopo E, Calignano A, Giordano F, Bolognese A. Synthesis and antihistaminic activity of some thiazolidin-4-ones. Journal of Medicinal Chemistry. 1992; 35(15):2910-2912. doi:10.1021/jm00093a025
23.    Appalanaidu K, Kotcherlakota R, Dadmal TL, Bollu VS, Kumbhare RM, Patra CR. Synthesis and biological evaluation of novel 2-imino-4-thiazolidinone derivatives as potent anti-cancer agents. Bioorganic & Medicinal Chemistry Letters. 2016; 26(21):5361-5368. doi:10.1016/j.bmcl.2016.08.013
24.    Ture A, Ergul M, Ergul M, Altun A, Kucukguzel İ. Design, synthesis, and anticancer activity of novel 4-thiazolidinone-phenylaminopyrimidine hybrids. Molecular Diversity. Published online April 23, 2020. doi:10.1007/s11030-020-10087-1
25.    Szychowski KA, Leja ML, Kaminskyy DV, et al. Study of novel anticancer 4-thiazolidinone derivatives. Chemico-Biological Interactions. 2017; 262:46-56. doi:10.1016/j.cbi.2016.12.008
26.    Senkardes S, Kucukguzel S. Recent Progress on Synthesis and Anticancer Activity of 4-Thiazolidinone. Mini-Reviews in Organic Chemistry. 2016; 13(5):377-388. doi:10.2174/1570193x13666160826154159
27.    Rawal RK, Prabhakar YS, Katti SB, De Clercq E. 2-(Aryl)-3-furan-2-ylmethyl-thiazolidin-4-ones as selective HIV-RT Inhibitors. Bioorganic & Medicinal Chemistry. 2005; 13(24):6771-6776. doi:10.1016/j.bmc.2005.07.063
28.    Kato T, Ozaki T, Tamura K, Suzuki Y, Akima M, Ohi N. Novel Calcium Antagonists with Both Calcium Overload Inhibition and Antioxidant Activity. 2. Structure−Activity Relationships of Thiazolidinone Derivatives. Journal of Medicinal Chemistry. 1999; 42(16):3134-3146. doi:10.1021/jm9900927
29.    Kato T, Ozaki T, Ohi N. Improved synthetic methods of CP-060S, a novel cardioprotective drug. Tetrahedron: Asymmetry. 1999; 10(20):3963-3968. doi:10.1016/s0957-4166(99)00441-3
30.    Adachi Y, Suzuki Y, Homma N, et al. The anti-ischemic effects of CP-060S during pacing-induced ischemia in anesthetized dogs. European Journal of Pharmacology. 1999; 367(2-3):267-273. doi:10.1016/s0014-2999(98)00938-8
31.    Ottana R, Mazzon E, Dugo L, et al. Modeling and biological evaluation of 3,3′-(1,2-ethanediyl)bis[2-(4-methoxyphenyl)-thiazolidin-4-one], a new synthetic cyclooxygenase-2 inhibitor. European Journal of Pharmacology. 2002; 448(1):71-80. doi:10.1016/s0014-2999(02)01888-5
32.    Tanabe Y, Yamamoto H, Murakami M, et al. Synthetic study of the highly potent and selective anti-platelet activating factor thiazolidin-4-one agents and related compounds. Journal of the Chemical Society, Perkin Transactions 1. 1995; (7):935. doi:10.1039/p19950000935
33.    Swathi K, Sreenivasulu M, Reddy THN, Kumar Y, Mahaboob Basha G. A Review on 1,3-Thiazolidin-4-Ones. Asian Journal of Research in Chemistry. 2013; 6(10).
34.    C P, Bhalgat C, Chitale S, Ramesh B. Synthesis and Biological Activities of Some Novel Heterocyclic Compounds Containing Thiazolidinone Derivatives. Research Journal of Pharmacy and Technology. 2011; 4(6)
35.    Sahu R, Dash S, Garnaik BK. Thermal, spectral, antibacterial and antioxidant studies on inclusion complexes of 2-(Benzothiazolyl-2’)hydrazono-3-phenyl 5-arylidene-4-Thiazolidinone derivatives with β-cyclodextrin. Research Journal of Pharmacy and Technology. 2016; 9(12):2265. doi:10.5958/0974-360x.2016.00457.1

Recomonded Articles:

Author(s): P. Valentina, K. Ilango, Deepak Jain, Prerna Shukla

DOI:         Access: Open Access Read More

Author(s): Tuly Paul, Faruk Hossen, Kudrat-E-Zahan, Masuqul Haque, Saddam Hossain, Rausan Zamir, Ali Asraf

DOI: 10.5958/0974-4150.2020.00052.8         Access: Open Access Read More

Author(s): Shravani S. Pawar, Sachin H. Rohane

DOI: 10.5958/0974-4150.2021.00014.6         Access: Open Access Read More

Author(s): Hunasnalkar Shivraj G, Shaikh Gazi, Patil SM, Surwase Ulhas S

DOI:         Access: Open Access Read More

Author(s): SR Pattan, NS Dighe, SA Nirmal, AN Merekar, RB Laware, HV Shinde, DS Musmade

DOI:         Access: Open Access Read More

Author(s): Pankaj Baboo, Girendra Gautam, S.K. Gupta

DOI: 10.5958/0974-4150.2017.00039.6         Access: Open Access Read More

Author(s): Sindhu. T. J, Akhilesh K. J, Anju. Jose, Binsiya K. P, Blessy Thomas, Elizabeth Wilson

DOI: 10.5958/0974-4150.2020.00026.7         Access: Open Access Read More

Author(s): KP Bhusari, ND Amnerkar, PB Khedekar, MK Kale, RP Bhole

DOI:         Access: Open Access Read More

Author(s): S. Ganapathy, G.V.H. Raju, D.G. Sankar, Pettla Y. Naidu

DOI:         Access: Open Access Read More

Author(s): Sushil Kumar Dubey, Amla Batra

DOI:         Access: Open Access Read More

Author(s): Virupakshi Prabhakar, Kondra Sudhakar Babu, L.K. Ravindranath, J. Latha, B.Venkateswarlu

DOI: 10.5958/0974-4150.2017.00011.6         Access: Open Access Read More

Author(s): N V L Suvarchala Reddy V, Sneha J Anarthe, Ganga Raju M, Akhila M, Pooja Raj G.B.

DOI: 10.5958/0974-4150.2019.00020.8         Access: Open Access Read More

Author(s): S. N. Battin, A. H. Manikshete, S. K. Sarasamkar, M. R. Asabe, D. J. Sathe

DOI: 10.5958/0974-4150.2017.00112.2         Access: Open Access Read More

Author(s): Gupta Akhilesh, Rawat Swati

DOI:         Access: Open Access Read More

Author(s): Sabale Prafulla, Potey Lata, Rahangdale Priya, Sabale Vidya

DOI: 10.5958/0974-4150.2019.00011.7         Access: Open Access Read More

Author(s): Kishore Kumar Valluri, Tejeswara Rao Allaka, I V Kasi Viswanath, Nagaraju PVVS

DOI: 10.5958/0974-4150.2018.00111.6         Access: Open Access Read More

Author(s): Firke SD, Firake BM, Chaudhari RY, Patil VR

DOI:         Access: Open Access Read More

Asian Journal of Research in Chemistry (AJRC) is an international, peer-reviewed journal devoted to pure and applied chemistry..... Read more >>>

RNI: Not Available                     
DOI: 10.5958/0974-4150 

Popular Articles


Recent Articles




Tags