Liquid-assisted grinding (LAG) approach, metal-free synthesis of 2,3-dihydro-1,5-benzothiazepines and their electrochemical properties
Manjit Singh A , Kuldeep Kumar Maurya A and Manisha Malviya A *A
Abstract
In this work, we have disclosed a facile metal-free synthesis of pharmaceutically fascinating and biologically important benzothiazepines in the presence of a few drops of ethanol. The present methodology converts chalcones and ortho-amino thiophenol into 2,3-dihydro-1,5-benzothiazepines under ambient conditions using liquid-assisted grinding, resulting in rapid synthesis in a very short period. This process is eco-friendly, operationally simple and gives good to excellent yields of products with easy isolation. This approach offers a facile synthesis of 2,3-dihydro-1,5-benzothiazepines from three readily available starting materials. An electrochemical study of the benzothiazepine derivatives was undertaken using cyclic voltammetry and electrochemical impedance spectroscopy techniques.
Keywords: benzothiazepine, cyclic voltammetry, diffusion coefficient, electrochemical impedance spectroscopy, grinding assisted, mechanochemistry, metal free, one-pot synthesis.
References
1 James SL, Adams CJ, Bolm C, Braga D, Collier P, Friščić T, Grepioni F, Harris KD, Hyett G, Jones W, Krebs A, Mack J, Maini L, Orpen AG, Parkin IP, Shearouse WC, Steed JW, Waddell DC. Mechanochemistry: opportunities for new and cleaner synthesis. Chem Soc Rev 2012; 41: 413-447.
| Crossref | Google Scholar | PubMed |
2 Micheli F, Degiorgis F, Feriani A, Paio A, Pozzan A, Zarantonello P, Seneci P. A combinatorial approach to [1,5]benzothiazepine derivatives as potential antibacterial agents. J Comb Chem 2001; 3: 224-228.
| Crossref | Google Scholar | PubMed |
4 Verma P, Chauhan S, Singh V, Singh S, Srivastava V. Urea hydrogen peroxide-initiated synthesis of pyranopyrazoles through oxidative coupling under base- and metal-free conditions by physical grinding method. Mol Divers 2022; 26: 1769-1777.
| Crossref | Google Scholar | PubMed |
5 Ying P, Yu J, Su W. Liquid-assisted grinding mechanochemistry in the synthesis of pharmaceuticals. Adv Synth Catal 2021; 363: 1246-1271.
| Crossref | Google Scholar |
6 Mahata A, Bhaumick P, Panday AK, Yadav R, Parvin T, Choudhury LH. Multicomponent synthesis of diphenyl-1,3-thiazole-barbituric acid hybrids and their fluorescence property studies. New J Chem 2020; 44: 4798-4811.
| Crossref | Google Scholar |
7 Su X, Su W, Wang Y, Wang Y, Ming X, Kong Y. The pyrrolidinoindoline alkaloid Psm2 inhibits platelet aggregation and thrombus formation by affecting PI3K/Akt signaling. Acta Pharmacol Sin 2016; 37: 1208-1217.
| Crossref | Google Scholar | PubMed |
8 Ansari FL, Kalsoom S, Zaheer-ul-Haq Z, Ali Z, Jabeen F. In silico studies on 2,3-dihydro-1,5-benzothiazepines as cholinesterase inhibitors. Med Chem Res 2012; 21: 2329-2339.
| Crossref | Google Scholar |
9 Bariwal JB, Upadhyay KD, Manvar AT, Trivedi JC, Singh JS, Jain KS, Shah AK. 1,5-Benzothiazepine, a versatile pharmacophore: a review. Eur J Med Chem 2008; 43: 2279-2290.
| Crossref | Google Scholar | PubMed |
10 Saini RK, Joshi YC, Joshi P. Solvent-free synthesis of some 1,5-benzothiazepines and benzodiazepines and their antibacterial activity. Phosphorus Sulfur Silicon Relat Elem 2008; 9: 2181-2190.
| Crossref | Google Scholar |
11 Pieper GM, Siebeneich W. Temocapril, an angiotensin converting enzyme inhibitor, protects against diabetes-induced endothelial dysfunction. Eur J Pharmacol 2000; 403: 129-132.
| Crossref | Google Scholar | PubMed |
12 Arakawa M, Sasaki M, Ohmori M, Harada K, Fujimura A. Pharmacokinetics and pharmacodynamics of temocapril during repeated dosing in elderly hypertensive patients. Eur J Clin Pharmacol 2001; 56: 775-779.
| Crossref | Google Scholar | PubMed |
13 Muthusamy S, Kumar MDS, Suresh E. Synthesis of indole annulated [1,3]-thiazaheterocycles and -macrocycles via ring-closing metathesis. ChemistrySelect 2016; 1: 2603-2609.
| Crossref | Google Scholar |
14 Niu X, Yang B, Li Y, Fang S, Huang Z, Xie C, Ma C. A transition metal-free tandem process to pyridazinopyrido[3,2-f][1,4]thiazepine-diones via Smiles rearrangement. Org Biomol Chem 2013; 11: 4102-4108.
| Crossref | Google Scholar | PubMed |
15 Kawakita S, Kinoshita M, Ishikawa H, Kagoshima T, Katori R, Ishikawa K, Hirota Y. Efficacy and safety of clentiazem in patients with essential hypertension: results of an early pilot test. Clin Cardiol 1991; 14: 53-60.
| Crossref | Google Scholar | PubMed |
16 Berry R, Turner P. The pathology of a cross-over trial (Thiazesim—a new anti-depressant drug). Br J Psychiatry 1968; 114: 203-206.
| Crossref | Google Scholar | PubMed |
17 Ye N, Neumeyer JL, Baldessarini RJ, Zhen X, Zhang A. Update 1 of: recent progress in development of dopamine receptor subtype-selective agents: potential therapeutics for neurological and psychiatric disorders. Chem Rev 2013; 113: PR123-PR178.
| Crossref | Google Scholar |
18 Chate AV, Joshi RS, Mandhane PG, Gill CH. An improved procedure for the synthesis of 1,5-benzothiazepines using ceric ammonium nitrate (CAN). J Korean Chem Soc 2011; 55: 776-780.
| Crossref | Google Scholar |
19 Pan X-Q, Zou J-P, Huang Z-H, Zhang W. Ga(OTf)3-promoted condensation reactions for 1,5-benzodiazepines and 1,5-benzothiazepines. Tetrahedron Lett 2008; 49: 5302-5308.
| Crossref | Google Scholar |
20 Kodomari M, Noguchi T, Aoyama T. Solvent‐free synthesis of 1,5‐benzothiazepines and benzodiazepines on inorganic supports. Synth Commun 2004; 34(10): 1783-1790.
| Crossref | Google Scholar |
21 Ali P, Meshram J, Sheikh J, Tiwari V, Dongre R, Hadda TB. Predictions and correlations of structure activity relationship of some aminoantipyrine derivatives on the basis of theoretical and experimental ground. Med Chem Res 2012; 21: 157-164.
| Crossref | Google Scholar |
22 Sharma G, Kumar R, Chakraborti AK. Fluoroboric acid adsorbed on silica-gel (HBF4–SiO2) as a new, highly efficient and reusable heterogeneous catalyst for thia-Michael addition to α,β-unsaturated carbonyl compounds. Tetrahedron Lett 2008; 49: 4272-4275.
| Crossref | Google Scholar |
23 Singh M, Yadav VB, Ansari MD, Malviya M, Siddiqui IR. Efficient one-pot synthesis of substituted diphenyl 1, 3-thiazole through multicomponent reaction by using green and efficient Iron-catalyst via Cross-Dehydrogenative Coupling (CDC). Mol Divers 2022; 26: 843-848.
| Crossref | Google Scholar | PubMed |
24 Pinate P, Makone S. Synthesis and study of catalytic perspectives of DABCO based ionic liquid for the synthesis of 2,3-dihydro-1,5-benzothiazepines and 2-phenylbenzothiazoles. Catal Lett 2022; 153: 995-1012.
| Crossref | Google Scholar |
25 Devi V, Singh G, Monga V. Recent advances in the synthetic chemistry of 1,5-benzothiazepines: a minireview. J Heterocycl Chem 2020; 57(9): 3255-3270.
| Crossref | Google Scholar |
26 Albanese DCM, Gaggero N, Fei M. A practical synthesis of 2,3-dihydro-1,5-benzothiazepines. Green Chem 2017; 19(23): 5703-5707.
| Crossref | Google Scholar |
27 Yadav N, Yadav VB, Ansari MD, Sagir H, Verma A, Siddiqui IR. Catalyst-free synthesis of 2,3-dihydro-1,5-benzothiazepines in a renewable and biodegradable reaction medium. New J Chem 2019; 43(18): 7011-7014.
| Crossref | Google Scholar |
28 Chalkley MJ, Del Castillo TJ, Matson BD, Roddy JP, Peters JC. Catalytic N2-to-NH3 conversion by Fe at lower driving force: a proposed role for metallocene-mediated PCET. ACS Cent Sci 2017; 3: 217-223.
| Crossref | Google Scholar | PubMed |
29 Harris KDM. How grinding evolves. Nat Chem 2013; 5: 12-14 –1214.
| Crossref | Google Scholar |
30 Yamada H, Yoshii K, Asahi M, Chiku M, Kitazumi Y. Cyclic voltammetry. Part 1: fundamentals. Electrochemistry 2022; 90(10): 102005.
| Crossref | Google Scholar |
31 Naggar AH, El Kaoutit M, Naranjo-Rodriguez I, El-Sayed AY, Hidalgo-Hidalgo de Cisneros JL. Voltammetric and spectroscopic investigation of the interaction between 1,4-benzodiazepines and bovine serum albumin. J Solution Chem 2016; 45: 1659-1678.
| Crossref | Google Scholar |
32 Direksilp C, Scheiger JM, Ariyasajjamongkol N, Sirivat A. A highly selective and sensitive electrochemical sensor for dopamine based on a functionalized multi-walled carbon nanotube and poly(N-methylaniline) composite. Anal Methods 2022; 14(4): 469-479.
| Crossref | Google Scholar | PubMed |
33 Kalagi SS, Mali SS, Dalavi DS, Inamdar AI, Im H, Patil PS. Transmission attenuation and chromic contrast characterization of R.F. sputtered WO3 thin films for electrochromic device applications. Electrochim Acta 2012; 85: 501-508.
| Crossref | Google Scholar |
35 Nicholson C. Anomalous diffusion inspires anatomical insights. Biophys J 2015; 108(9): 2091-2093.
| Crossref | Google Scholar |
36 Elugoke SE, Fayemi OE, Adekunle AS, Ganesh PS, Kim SY, Ebenso EE. Sensitive and selective neurotransmitter epinephrine detection at a carbon quantum dots/copper oxide nanocomposite. J Electroanal Chem 2023; 929: 117120.
| Crossref | Google Scholar |