Login Register Cart 0
Generic placeholder image

Mini-Reviews in Medicinal Chemistry

Editor-in-Chief

ISSN (Print): 1389-5575
ISSN (Online): 1875-5607

Back
Journal Home About Journal Editorial Board Journal Insight Current Issue Volumes/Issues
Subscribe
Mini-Review Article

Novel GABAA Agonist Entities: Pharmacological Investigation and Molecular Modeling Study of Thiazolo- and Thiadiazolo-[3,2-a][1,3]diazepine Analogs

Author(s): Hussein I. El-Subbagh*

Volume 21, Issue 9, 2021

Published on: 30 December, 2020

Page: [1048 - 1057] Pages: 10

DOI: 10.2174/1389557521999201230195733

Price: $65

Abstract

Thiazolo- and thiadiazolo-[3,2-a][1,3]diazepines and their patented derivatives, tested with diverse CNS pharmacological activities, constitute an important class of compounds for new drug development. Therefore, research efforts were continued to design, synthesize, and evaluate compounds for their ultra-short, short-acting hypnotic, anticonvulsant, and neuromuscular blocking activities. The present review provides a summary of the work accomplished by these heterocycles and their biological evaluation.

Keywords: Thiazolo[3, 2-a][1, 3]diazepines, thiadiazolo[3, 2-a][1, 3]diazepines, ultra-short-acting hypnotics, short-acting hypnotics, anticonvulsants, neuromuscular blockers, molecular modeling studies.

« Previous Next »
Graphical Abstract

[1]
Kieć-Kononowicz, K.; Karolak-Wojciechowska, J.; Michalak, B.; Pekala, E.; Schumacher, B.; Müller, C.E. Imidazo[2,1-b]thiazepines: Synthesis, structure and evaluation of benzodiazepine receptor binding. Eur. J. Med. Chem., 2004, 39(3), 205-218.
[http://dx.doi.org/10.1016/j.ejmech.2003.11.009] [PMID: 15051168]
[2]
Zhu, M.; Wu, X.; Sang, L.; Fan, F.; Wang, L.; Wu, X.; Hua, R.; Wang, Y.; Lib, Q.X. A novel and effective benzo[d]thiazole-based fluorescent probe with dual recognition factors for highly sensitive and selective imaging of cysteine in vitro and in vivo. Sci. Total Environ., 2019, 43, 13463-13470.
[3]
Wanga, Y.; Wanga, L.; Zhua, M.; Xuea, J.; Huaa, R.; Lib, Q.X. Comparative studies on biophysical interactions between gambogic acid and serum albumin via multispectroscopic approaches and molecular docking. J. Lumin., 2019, 205, 210-218.
[http://dx.doi.org/10.1016/j.jlumin.2018.09.005]
[4]
Zhu, M.; Wang, L.; Zhang, H.; Fan, S.; Wang, Z.; Li, Q.X.; Wang, Y.; Liu, S. Interactions between tetrahydroisoindoline-1,3-dione derivatives and human serum albumin via multiple spectroscopy techniques. Environ. Sci. Pollut. Res. Int., 2018, 25(18), 17735-17748.
[http://dx.doi.org/10.1007/s11356-018-1955-9] [PMID: 29671232]
[5]
Zhu, M.; Wang, L.; Wang, Y.; Zhou, J.; Ding, J.; Li, W.; Xin, Y.; Fan, S.; Wang, Z.; Wang, Y. Biointeractions of herbicide atrazine with human serum albumin: UV-vis, fluorescence and circular dichroism approaches. Int. J. Env. Res. Pub. He., 2018, 15(1), 116.
[6]
Imming, P. Synthesis of the first penicillin derivatives with medium-sized lactam ring and of related thiazolidines. Arch. Pharm. (Weinheim), 1995, 328, 207-215.
[http://dx.doi.org/10.1002/ardp.19953280302]
[7]
Ueda, T.; Doi, W.; Nagai, S.I.; Sakakibara, J. Synthesis of [1,2,5]selena(or thia)diazolo[3,4-e]-[1,4]diazepines, [1,2,5]selena(or thia)diazolo[3,4-e][1,4]oxazepines and [1,2,5]selena(or thia) diazolo[3,4-c][1,2,6]thiadiazines. J. Heterocycl. Chem., 2000, 37, 1269-1272.
[http://dx.doi.org/10.1002/jhet.5570370540]
[8]
Pissiotas, G.; Moser, H.; Brunner, H. Herbicidal 1H,3H,5H-[1,3,4]thiadiazolo[3,4-a][1,2]di-azepin-1-ones and analogs. PCT Int. Appl. WO, 9500521 A119950105. 1995.
[9]
Marshall, B.E.; Longnecker, D.E. General Anesthetics.The Pharmacological Basis of Therapeutics, 9th ed; J. G, Hardman; L. E, Limbird, Eds.; McGraw-Hill: New York,; , 1996, pp. 321-323.
[10]
Shapiro, H.M. Intracranial hypertension: Therapeutic and anesthetic considerations. Anesthesiology, 1975, 43(4), 445-471.
[http://dx.doi.org/10.1097/00000542-197510000-00010] [PMID: 1101754]
[11]
Shader, R.I.; Greenblatt, D.J. Use of benzodiazepines in anxiety disorders. N. Engl. J. Med., 1993, 328(19), 1398-1405.
[http://dx.doi.org/10.1056/NEJM199305133281907] [PMID: 8292115]
[12]
Saab, R.N. Anesthesia for the premature infant.Middle East J. Anaesthesiol.,, 2004, 17(4), 723-744.
[PMID: 15255669]
[13]
Eilers, H.; Niemann, C. Clinically important drug interactions with intravenous anaesthetics in older patients. Drugs Aging, 2003, 20(13), 969-980.
[http://dx.doi.org/10.2165/00002512-200320130-00002] [PMID: 14561101]
[14]
Hardman, J.; Limbird, L.E.; Hardman, J.; Limbird, L.E. Goodman & Gilman’s the pharmacological basis of therapeutics; McGraw-Hill Medical Pub; Division: New York, 2001, pp. 315-319.
[15]
Naguib, M.; Magboul, M.M.; Samarkandi, A.H.; Attia, M. Adverse effects and drug interactions associated with local and regional anaesthesia. Drug Saf., 1998, 18(4), 221-250.
[http://dx.doi.org/10.2165/00002018-199818040-00001] [PMID: 9565736]
[16]
Khan-Ghori, S.N.; Murshid, W.R.; Samarkandi, A.H.; Al-Salman, M.; Salih, M.A. Use of propofol and sevoflurane in moyamoya disease-case reports and literature review.Middle East J. Anaesthesiol.,, 1999, 15(1), 73-83.
[PMID: 10068972]
[17]
Rang, H.P.; Dale, M.M.; Ritter, J.M. General anesthetic agents. Pharmacology, 5th ed; Churchill Livingstone: New York, 2005, pp. 503-515.
[18]
Rang, H.P.; Dale, M.M.; Ritter, J.M. Anxiolytic and hypnotic drugs. Pharmacology, 5th ed; Churchill Livingstone: New York, 2005, pp. 515-527.
[19]
Marshall, B.E.; Hanson, C.W.; Marshall, C. Clinical physiology and pathophysiology of the respiratory system. A Practice of Anesthesia; Healy, D; Cohen, P.J., Ed.; Edward Arnold: London, 1995, pp. 119-145.
[20]
El-Subbagh, H.I.; El-Kashef, H.A.; Kadi, A.A.; Abdel-Aziz, A.A-M.; Hassan, G.S.; Tettey, J.; Lehmann, J. New ultra-short acting hypnotic: Synthesis, biological evaluation, and metabolic profile of ethyl 8-oxo-5,6,7,8-tetrahydro-thiazolo[3,2-a][1,3]diazepin-3-carbo-xylate (HIE-124). Bioorg. Med. Chem. Lett., 2008, 18(1), 72-77.
[http://dx.doi.org/10.1016/j.bmcl.2007.11.011] [PMID: 18023180]
[21]
Kadi, A.A.; El-Kashef, H.A.; Abdel-Aziz, A.A-M.; Hassan, G.S.; Tettey, J.; Grant, M.H.; Lehmann, J.; El-Subbagh, H.I. Synthesis, ultra-short acting hypnotic activity, and metabolic profile of ethyl 8-oxo-5,6,7,8-tetrahydro-thiazolo[3,2-a] [1,3]diazepin-3-carboxylate (HIE-124). Arch. Pharm. (Weinheim), 2008, 341(2), 81-89.
[http://dx.doi.org/10.1002/ardp.200700132] [PMID: 18214840]
[22]
Lehmann, J.; El-Subbagh, H.I.; El-Kashef, H.A. Neue schnell wirkende Anesthetika. New ultra-short acting hypnotics. German Patent DE 103 20 732 A1, 2004.
[23]
Abourashed, E.A.; Hefnawy, M.M. H.I., El-Subbagh HPTLC analysis of a new ultra-short-acting thiazolodiazepine hypnotic (HIE-124) in spiked human plasma. J. Planar Chromatog., 2009, 22, 183-186.
[http://dx.doi.org/10.1556/JPC.22.2009.3.4]
[24]
Hefnawy, M.; Al-Omar, M.; Julkhuf, S.; Attia, S.; Abourashed, E.; El-Subbagh, H. Novel, selective sample stacking microemulsion electrokinetic capillary chromatography induced by reverse migrating pseudostationary phase for the determination of the new ultra-short acting hypnotic “HIE-124” in mice serum. Anal. Chim. Acta, 2010, 673(2), 194-199.
[http://dx.doi.org/10.1016/j.aca.2010.05.030] [PMID: 20599035]
[25]
Kadi, A.; Hefnawy, M.; Al-Majed, A.; Alonezi, S.; Asiri, Y.; Attia, S.; Abourashed, E.; El-Subbagh, H. Liquid chromatographic high-throughput analysis of the new ultra-short acting hypnotic ‘HIE-124’ and its metabolite in mice serum using a monolithic silica column. Analyst (Lond.), 2011, 136(3), 591-597.
[http://dx.doi.org/10.1039/C0AN00381F] [PMID: 21079880]
[26]
Al-Rashood, S.T.A.; Hassan, G.S.; El-Messery, S.M.; El-Taher, K.E.H.; Hefnawy, M.M.; Al-Omar, M.A.; El-Subbagh, H.I. Synthesis, biological evaluation and molecular modeling study of some new thiazolodiazepine analogs as CNS active agents. Bioorg. Med. Chem. Lett., 2016, 26(2), 445-453.
[http://dx.doi.org/10.1016/j.bmcl.2015.11.097] [PMID: 26706170]
[27]
Al-Rashood, S.T.A.; El-Subbagh, H.I.; Hassan, G.S.; El-Taher, K.E.H.; Al-Omar, M.A. Thiazolo[3,2-a][1,3]diazepine derivatives and pharmaceutical compositions containing the same as novel anticonvulsant agents and method for their preparation. Europ. Pat. EP 2 592 085 B1., 2016.
[28]
El-Subbagh, H.I.; Hassan, G.S.; El-Azab, A.S.; Abdel-Aziz, A.A-M.; Kadi, A.A.; Al-Obaid, A.M.; Al-Shabanah, O.A.; Sayed-Ahmed, M.M. Synthesis and anticonvulsant activity of some new thiazolo[3,2-a][1,3]diazepine, benzo[d]thiazolo[5,2-a][12,6]diazepine and benzo[d]oxazolo[5,2-a][12,6]diazepine analogues. Eur. J. Med. Chem., 2011, 46(11), 5567-5572.
[http://dx.doi.org/10.1016/j.ejmech.2011.09.021] [PMID: 21963116]
[29]
Hassan, G.S.; El-Subbagh, H.I.; Al-Omar, M.A.; El-Taher, K.E.H.; Al-Rashood, K.A.; Al-Obaid, A.M.; Al-Azab, A.S.; Abdelaziz, A.A-M.; Al-Omary, F.A.; Hefnawy, M.M. 6,7-Dihydro-[1,3,4]thiadiazolo-[3,2-a][1,3]diazepin derivatives and pharmaceutical compositions containing the same as hypnotic or anesthetic agent and method for their preparation Europ. Pat. EP 2 514 753 B1,, 2013.
[30]
Hassan, G.S.; El-Subbagh, H.I.; Al-Omar, M.A.; El-Taher, K.E.H.; Al-Rashood, K.A.; Al-Obaid, A.M.; Al-Azab, A.S.; Abdelaziz, A.A-M.; Al-Omary, F.A.; Hefnawy, M.M. 6,7-Dihydro- [1,3,4]thiadiazolo-[3,2-a][1,3]diazepin derivatives and pharmaceutical compositions containing the same as hypnotic or anesthetic agent and method for their preparation United States patent US 8,741,893 B2,, 2014.
[31]
Fredholm, B-B.; Persson, C.G. Xanthine derivatives as adenosine receptor antagonists. Eur. J. Pharmacol., 1982, 81(4), 673-676.
[http://dx.doi.org/10.1016/0014-2999(82)90359-4] [PMID: 6288418]
[32]
Janssen, P.A.J. 5-HT2 Receptor blockade to study serotonin-induced pathology. Trends Pharmacol. Sci., 1983, 4, 198-206.
[http://dx.doi.org/10.1016/0165-6147(83)90365-6]
[33]
Macdonald, R.L.; Twyman, R.E.G.; Ryan-Jastrow, T.; Angelotti, T.P. Regulation of GABAA receptor channels by anticonvulsant and convulsant drugs and by phosphorylation.Epilepsy Res. Suppl.,, 1992, 9, 265-277.
[PMID: 1337441]
[34]
Haefely, W. Antagonists of benzodiazepines: Functional aspects. Adv. Biochem. Psychopharmacol.,, 1983, 38, 73-93.
[PMID: 6142609]
[35]
File, S.E.; Pellow, S. Intrinsic actions of the benzodiazepine receptor antagonist Ro 15-1788. Psychopharmacology (Berl.), 1986, 88(1), 1-11.
[http://dx.doi.org/10.1007/BF00310505] [PMID: 3003778]
[36]
Brogdén, R.N.; Goa, K.L. Flumazenil. A preliminary review of its benzodiazepine antagonist properties, intrinsic activity and therapeutic use. Drugs, 1988, 35(4), 448-467.
[http://dx.doi.org/10.2165/00003495-198835040-00004] [PMID: 2839329]
[37]
El-Subbagh, H.I.; Hassan, G.S.; El-Taher, K.E.H.; El-Messery, S.M.; Al-Azab, A.S.; Abdelaziz, A.A-M.; Hefnawy, M.M. Synthesis, biological evaluation and molecular modeling study of thiadiazolo[3,2-a][1,3]diazepine analogues of HIE-124 as a new class of short acting hypnotics. Eur. J. Med. Chem., 2016, 124, 237-247.
[http://dx.doi.org/10.1016/j.ejmech.2016.08.038] [PMID: 27597405]
[38]
Al-Azab, A.S.; El-Subbagh, H.I.; Al-Rashood, K.A.; El-Taher, K.E.H.; Al-Omar, M.A.; Hassan, G.S.; Al-Omary, F.A.; Abdelaziz, A.A-M.; Hefnawy, M.A. 6,7-dihydro-[1,3,4]thiadiazolo-[3,2- a][1,3]diazepin derivative and pharmaceutical composition containing the same as neuromuscular blocker or skeletal muscle relaxant, and method for the preparation Europ. Pat. EP 2 514 754 B1,, 2013.
[39]
Al-Azab, A.S.; El-Subbagh, H.I.; Al-Rashood, K.A.; El-Taher, K.E.H.; Al-Omar, M.A.; Hassan, G.S.; Al-Omary, F.A.; Abdelaziz, A.A-M.; Hefnawy, M.A. 6,7-dihydro-[1,3,4]thiadiazolo-[3,2- a][1,3]diazepin derivative and pharmaceutical composition containing the same as neuromuscular blocker or skeletal muscle relaxant, and method for the preparation United States patent US 8,846,665 B2,, 2014.
[40]
Henning, R.H.; Nelemans, A.; Houwertjes, M.; Agoston, S. Reversal by suramin of neuromuscular block produced by pancuronium in the anaesthetized rat. Br. J. Pharmacol., 1993, 108(3), 717-720.
[http://dx.doi.org/10.1111/j.1476-5381.1993.tb12867.x] [PMID: 8467359]
[41]
Thesleff, S.; Unna, K.R. .Differences in mode of neuromuscular blockade in a series of symmetric bis-quaternary ammonium salts. J. Pharmacol. Exp. Ther.,, 1954, 111(1), 99-113.
[PMID: 13163849]
[42]
Buttle, G.A.H.; Zamis, E.J. The action of decamethonium in birds. J. Pharm. Pharmacol., 1949, 1, 991-992.
[http://dx.doi.org/10.1111/j.2042-7158.1949.tb12517.x]
[43]
Mowrey, D.D.; Liu, Q.; Bondarenko, V.; Chen, Q.; Seyoum, E.; Xu, Y.; Wu, J.; Tang, P. Insights into distinct modulation of α7 and α7β2 nicotinic acetylcholine receptors by the volatile anesthetic isoflurane. J. Biol. Chem., 2013, 288(50), 35793-35800.
[http://dx.doi.org/10.1074/jbc.M113.508333] [PMID: 24194515]
[44]
El-Subbagh, H.I.; El-Azab, A.S.; Hassan, G.S.; El-Messery, S.M.; Abdel-Aziz, A.A-M.; El-Taher, K.E.H. Thiadiazolodiazepine analogues as a new class of neuromuscular blocking agents: Synthesis, biological evaluation and molecular modeling study. Eur. J. Med. Chem., 2017, 126, 15-23.
[http://dx.doi.org/10.1016/j.ejmech.2016.09.096] [PMID: 27744183]

Rights & Permissions Print Cite
Article Metrics
14
1
© 2024 Bentham Science Publishers | Privacy Policy