Synthesis of Heterocyclic Compounds Possessing the 4H‐Thieno[3,2‐b]pyrrole Moiety.

Ilyin, A.P.; Дмитриева, И. Г.; Kustova, Veronika A.; Manaev, Alexandre V.; Ivachtchenko, Alexandre V.

doi:10.1002/chin.200724107

Cited by 4 publications

(5 citation statements)

References 1 publication

Supporting

Mentioning

Contrasting

Order By: Relevance

“…This indicates that the spectrum of its biological activity is fairly narrow, which is a highly desirable attribute in a potential lead compound. In addition, Ilyin et al [34] recently described a solution-phase strategy for the synthesis of novel combinatorial libraries containing a thieno[3,2- b ]pyrrole core, thus providing the opportunity to further explore and potentially exploit these compounds as therapeutics for a range of human diseases, including infections with neurotropic alphaviruses.…”

Section: Discussionmentioning

confidence: 99%

Identification of Thieno[3,2‐b]Pyrrole Derivatives as Novel Small Molecule Inhibitors of Neurotropic Alphaviruses

Peng¹,

Peltier

Larsen

et al. 2009

J INFECT DIS

View full text Add to dashboard Cite

Neurotropic alphaviruses such as western, eastern, and Venezuelan equine encephalitis viruses cause serious and potentially fatal central nervous system infections in humans and are high-priority potential bioterrorism agents. There are currently no widely available vaccines or licensed therapies for these virulent pathogens. To identify potential novel antiviral drugs, we developed a cell-based assay with a western equine encephalitis virus replicon that expresses a luciferase reporter gene and screened a small molecule diversity library of 51,028 compounds. We identified and validated a thieno[3,2-b]pyrrole compound with a half maximal inhibitory concentration of <10 µmol/L, a selectivity index >20, and potent activity against live virus in cultured neuronal cells. Furthermore, a structure-activity relationship analysis with 20 related compounds identified several with enhanced activity profiles, including 6 with submicromolar half maximal inhibitory concentrations. In conclusion, we have identified a novel class of promising inhibitors with potent activity against virulent neurotropic alphaviruses.

show abstract

Section: Discussionmentioning

confidence: 99%

Identification of Thieno[3,2‐b]Pyrrole Derivatives as Novel Small Molecule Inhibitors of Neurotropic Alphaviruses

Peng¹,

Peltier

Larsen

et al. 2009

J INFECT DIS

View full text Add to dashboard Cite

show abstract

“…General procedure for synthesis of thiosemicarbazide derivatives (11a-h) To a solution of 5.5 mmol of substituted acid hydrazides 9a or 9b in 30 mL of ethanol, 5.5 mmol of the appropriate aryl or alkylisothiocyanate 10 (isothiocyanatomethane, isothiocyanatobenzene, 1-isothiocyanato-4-methoxybenzene, 1-isothiocyanatonaphthalene, 1-isothiocyanato-4-nitrobenzene) was added. The mixture was refluxed for 3 h. The solid product, obtained on cooling, was washed with distilled water and recrystallized from ethanol to obtain compounds 11a-h (Ilyin et al, 2007). H 4.29, N 33.15, S 15.18, found: C 39.59, H 4.58, N 33.46, S 14.87.…”

Section: General Methodsmentioning

confidence: 99%

“…4 Synthesized compound 3d mapping a GluHypo10/1, b GluHypo4/4 (hydrogen bond acceptor as green vectored spheres, hydrophobic features as blue spheres, ring aromatic as orange vectored spheres, hydrogen bond donor as violet vectored spheres), and c Chemical structure of compound 3d (Color figure online) A solution of the thiosemicarbazide derivative 11a, 11c-f, or 11h (5.5 mmol) in 5 % sodium hydroxide solution (100 mL) was heated under reflux for 4 h. After cooling to room temperature, concentrated hydrochloric acid was added. The precipitate was filtered and washed several times with distilled water (Ilyin et al, 2007). The titled compounds were recrystallized from ethanol.…”

Section: General Methodsmentioning

confidence: 99%

Tryptophan and thiosemicarbazide derivatives: design, synthesis, and biological evaluation as potential β-d-galactosidase and β-d-glucosidase inhibitors

et al. 2014

View full text Add to dashboard Cite

Glycosidases, including b-D-galactosidase and b-D-glucosidase, are involved in a range of metabolic disorders, such as cancer, viral or bacterial infections, and diabetes. Previously, we scanned the pharmacophoric space of these enzymes and had a self-consistent and predictive quantitative structure-activity relationship that was used to identify several b-D-galactosidase and b-D-glucosidase inhibitors via in silico search of structural databases. Guided by the preceding modeling efforts, synthesis of a series of tryptophan and thiosemicarbazide derivatives as b-Dgalactosidase and b-D-glucosidase inhibitors that match the generated pharmacophores followed by in vitro bioassay was carried out. Synthesized compounds 3c (37 % inhibition at 100 lM) and 4d (49 % inhibition at 100 lM) exhibited the best inhibitory bioactivities against b-Dgalactosidase and b-D-glucosidase, respectively. They can serve as a promising lead compounds for the development of potential glycosidase inhibitors.

show abstract

“…Furo [3,2-b]pyrroles (V, Figure 3) and their thieno-and selenopheno-analogues are isosteres of the indole ring system in which the benzene ring is replaced by the furan, thiophene or selenophene rings. Efficient synthetic routes to these heterocycles are of great interest [17][18][19] because of their significant biological activity. 4H-Furo [3,2-b]pyrrole derivatives have been screened for their analgesic and anti-inflammatory activity [20], or antituberculotic [21] activity.…”

Section: Furo- Thieno-and Selenopheno [32-b]pyrrolesmentioning

confidence: 99%

Hemetsberger–Knittel and Ketcham Synthesis of Heteropentalenes with Two (1:1), Three (1:2)/(2:1) and Four (2:2) Heteroatoms

et al. 2023

View full text Add to dashboard Cite

The synthetic methods leading to furo[3,2-b]pyrroles and thiazolo [5,4-d]thiazoles are reviewed herein. Furo-, thieno- and seleno [3,2-b]pyrroles are related to heteropentalenes, containing two heteroatoms in the entire structure, one each per core. The synthetic approach follows the Hemetsberger–Knittel protocol covering three reaction steps—the nucleophilic substitution of halogen-containing aliphatic carboxylic acid esters, Knoevenagel condensation and, finally, thermolysis promoting the intramolecular cyclocondensation to O,N-heteropentalene. The Hemetsberger–Knittel reaction sequence is also known for the preparation of O,N-heteropentalenes with three heteroatoms (2:1) and their sulphur and selen heteroatoms containing structural analogues and bispyrroles. The synthetic approach towards thiazolo [5,4-d] thiazoles represents a more straightforward route, according to the Ketcham cyclocondensation. Proceeding with the Ketcham process is more challenging since it occurs stepwise and the formation of by-products is obvious. Thiazolo [5,4-d]thiazole is a representative of the aromatic heteropentalene with four heteroatoms in the structure—twinned N and S, two for each of the five-membered rings. The synthetic approaches towards those particular heteropentalnes have been chosen as a consequence of our ongoing research dealing with the design, synthesis and applications of substituted furo [3,2-b]pyrroles and thiazolo [5,4-d]thiazole-based derivatives. While the furopyrroles are known for their pharmacological activity, thiazolothiazoles have become of interest to materials science. We are aware that from a “bank” of existing compounds/procedures not all are presented in this review, and we apologise to respective groups whose research have not been objectively included.

show abstract

Synthesis of Heterocyclic Compounds Possessing the 4H‐Thieno[3,2‐b]pyrrole Moiety.

Cited by 4 publications

References 1 publication

Identification of Thieno[3,2‐b]Pyrrole Derivatives as Novel Small Molecule Inhibitors of Neurotropic Alphaviruses

Identification of Thieno[3,2‐b]Pyrrole Derivatives as Novel Small Molecule Inhibitors of Neurotropic Alphaviruses

Tryptophan and thiosemicarbazide derivatives: design, synthesis, and biological evaluation as potential β-d-galactosidase and β-d-glucosidase inhibitors

Hemetsberger–Knittel and Ketcham Synthesis of Heteropentalenes with Two (1:1), Three (1:2)/(2:1) and Four (2:2) Heteroatoms

Contact Info

Product

Resources

About