Uses of 2-Amino-5,6-dihydro-4H-cyclopenta [b] thiophene-3-carbonitrile in the Synthesis of Heterocyclic Compounds with Anticonvulsant, Behavioral and CNS Antidepressant Activities
K. A. El-Sharkawy, N. N. E. El-Sayed, M. Y. Zaki
International Research Journal of Pure and Applied Chemistry · pp. 91–104 · Published 23 May 2012
10.9734/IRJPAC/2012/1222Abstract
The reaction of the cyclopenta[b]thiophene derivative 3 with phenylisothiocyanate4 gave thiourea derivative 5. The latter was reacted with the active methylene reagents 2a, b and 7 to give pyrimidine derivatives 6a, b and 8. N-Acylation of compound 3 was achieved via its reaction with acetic anhydride 9 to give the acetyl derivative 10. Compound 10 was utilized as a key for the synthesis of different heterocyclic compounds, where arylidene derivative 12 was obtained via its reaction with benzaldehyde11 and thienopyridone derivative 13 was obtained via its intramolecular cyclization using basic catalysis. Finally treatment of 10 with different activated carbonitriles2a, b or with hydrazine derivatives 15a, b afforded thienopyridone derivatives 14a,b and thienopyrimidine derivatives 17a,b, respectively. The newly synthesized compounds were tested for anticonvulsant, behavioral and CNS antidepressant activities.
References (26)
- 1 Novel Alkaloids from the Sponge Batzella sp.: Inhibitors of HIV gp120-Human CD4 Binding [DOI]
- 2 Antiestrogens and Selective Estrogen Receptor Modulators as Multifunctional Medicines. 1. Receptor Interactions [DOI]
- 3 Antiestrogens and Selective Estrogen Receptor Modulators as Multifunctional Medicines. 2. Clinical Considerations and New Agents [DOI]
- 4 Phenobarbital for the Treatment of Epilepsy in the 21st Century: A Critical Review [DOI]
- 5 Antiestrogens. 2. Structure-activity studies in a series of 3-aroyl-2-arylbenzo[b]thiophene derivatives leading to [6-hydroxy-2-(4-hydroxyphenyl)benzo[b]thien-3-yl]-[4-[2-(1-piperidinyl)ethoxy]phenyl]methanone hydrochloride (LY 156758), a remarkably effective estrogen antagonist with only minimal intrinsic estrogenicity [DOI]
- 6 Regioselective reaction: Synthesis, characterization and pharmacological studies of some new Mannich bases derived from 1,2,4-triazoles [DOI]
- 7 A facile synthesis and antimycobacterial evaluation of novel spiro-pyrido-pyrrolizines and pyrrolidines [DOI]
- 8 Topical chemotherapy with 5-fluorouracil [DOI]
- 9 Synthesis of the tricyclic portions of batzelladines A, B and D. Revision of the stereochemistry of batzelladines A and D [DOI]
- 10 Evaluation of the semicarbazones, thiosemicarbazones and bis-carbohydrazones of some aryl alicycylic ketones for anticonvulsant and other biological propertie [DOI]
- 11 Optimization of the Central Heterocycle of α-Ketoheterocycle Inhibitors of Fatty Acid Amide Hydrolase [DOI]
- 12 Topically active carbonic anhydrase inhibitors. 2. Benzo[b]thiophenesulfonamide derivatives with ocular hypotensive activity [DOI]
- 13 Synthesis and antibacterial activity of 1H-pyrazolo[3,4-b]pyrazine and -pyridine derivatives [DOI]
- 14 Screening for antidepressant, sedative and analgesic activities of novel fused thiophene derivatives [DOI]
- 15 Synthesis of some new [1,2,4]triazolo[3,4-b][1,3,4]thiadiazines and [1,2,4]triazolo[3,4-b][1,3,4] thiadiazoles starting from 5-nitro-2-furoic acid and evaluation of their antimicrobial activity [DOI]
- 16 Synthesis of Novel 2,5‐Disubstituted 1,3,4‐Thiadiazoles for Their Potential Anticonvulsant Activity: Pharmacophoric Model Studies [DOI]
- 17 Synthesis and antiviral activity of novel [1,2,4]triazolo[3,4-b][1,3,4]thiadiazoles, [1,2,4]triazolo[3,4-b] [1,3,4]thiadiazines and [1,2,4]triazolo[3,4-b][1,3,4] thiadiazepines [DOI]
- 18 Synthesis and in vitro antitumoral activity of new 3,5-dicyanopyridine derivatives [DOI]
- 19 Novel benzothiophene-, benzofuran-, and naphthalenecarboxamidotetrazoles as potential antiallergy agents [DOI]
- 20 Synthesis and biological evaluation of 3-aryloxyalkyl-6-aryl-7H-s-triazolo[3,4-b][1,3,4]thiadiazines [DOI]
- 21 Synthesis, Analgesic, and Antiparkinsonian Profiles of Some Pyridine, Pyrazoline, and Thiopyrimidine Derivatives [DOI]
- 22 Synthesis and biological evaluation of 5-substituted benzo[b]thiophene derivatives as anti-inflammatory agents [DOI]
- 23 Malaria and the pregnant traveller [DOI]
- 24 Potential Broad Spectrum Anthelmintics IV: Design, Synthesis, and Antiparasitic Screening of Certain 3,6-Disubstituted- (7H) -s -triazolo- [3,4-b][1,3,4]thiadiazine Derivatives [DOI]
- 25 The reaction of β-amino-α,γ-dicyanocrotononitrile with acetophenone: Synthesis of pyridine, pyridazine and thiophene derivatives with antimicrobial activities [DOI]
- 26 Anti-Tumor and Anti-Leishmanial Evaluations of Novel Thiophene Derivatives Derived from the Reaction of Cyclopentanone with Elemental Sulphur and Cyano-Methylene Reagents [DOI]
Cited by 38
Nabil A. Alhakamy, Ahmad O. Noor, Khaled M. Hosny · Current Organic Synthesis · 2020
Madlen B. Labib, Phoebe F. Lamie · Medicinal Chemistry Research · 2016
Abhishek Kumar, Pankaj Kumar, Chaithanya P · Research Journal of Pharmacy and Technology · 2024
Sneha D. Satavalekar, Shashank T. Mhaske · Materials Today: Proceedings · 2018
Isha Mishra, Vikram Sharma, Nitin Kumar · Medicinal Chemistry · 2025
Anjaneyulu Bendi, Chanchal Vashisth, Poonam Devi · ChemistrySelect · 2025
Ahmed M. M. El-Saghier, Mehmet Akkurt, Shaaban K. Mohamed · Acta Crystallographica Section E Structure Reports Online · 2013
Gaurav Shukla, Keshav Raghuvanshi, Maya Shankar Singh · The Journal of Organic Chemistry · 2022
Salwa F. Mohamed, Eman R. Kotb, Eman A. Abd El-Meguid · Research on Chemical Intermediates · 2016
Noof A. Alenazi, Haifa Alharbi, Ahmad Fawzi Qarah · Arabian Journal of Chemistry · 2023
Showing 17 of 38 known citations — external sources report more than can currently be individually listed.
Related research
- Uses of 1-Cyanoacetyl-4-Phenyl-3-Thiosemicarbazide in the Synthesis of Antimicrobial and Antifungal Heterocyclic Compounds — shares topic coverage
- Synthesis and Antimicrobial Activity of Some New Coumarin Incorporated Pyridine-3-carbonitrile Derivatives — shares topic coverage
- Micellar Suzuki Cross-Coupling between Thiophene and Aniline in Water and under Air — shares topic coverage
- Thienothiophene Scaffolds as Building Blocks for (Opto)Electronics — shares topic coverage
- Looking for a Safe Bridge: Synthesis of P3HT-Bridge-TBO Block-Copolymers and Their Performance in Perovskite Solar Cells — shares topic coverage
Article metrics
Real usage data collected on this platform.
85
Page views
0
PDF downloads
32
Outbound clicks
38
Citations
Views over time
Views by country
Approximate, from request IP at view time — not citizenship or institution. Countries with fewer than 5 views are grouped as "Other".
Traffic sources
Referring site, by host.
Views and downloads exclude known bots/crawlers. Citations combines this platform's own DOI-resolved index with each external source's own reported total — see Cited by above for individually listed citing works. Last refreshed 0 seconds ago.