Non-Imidazole Histamine H3 Ligands, Part 2: New 2-Substituted Benzothiazoles as Histamine H3 Antagonists

Walczyński, Krzysztof; Guryn, Roman; Zuiderveld, Obbe P.; Timmerman, Henk

doi:10.1002/(sici)1521-4184(199911)332:11<389::aid-ardp389>3.0.co;2-u

Cited by 31 publications

(4 citation statements)

References 22 publications

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“…Previously we reported the synthesis and biological evaluation of 1-[(2-benzothiazole)-4-substituted]piperazine derivatives as non-imidazole histamine H 3 -receptor antagonists [29,30]. We showed that the most potent compounds (in vitro screening) at the model are the n-propyl-, i-propyl-and allylbenzothiazole derivatives (2; Chart 1) with pA 2 ¼ 7.16; 7.21; 7.10, respectively.…”

Section: Introductionsupporting

confidence: 56%

Non-imidazole histamine H3 ligands, Part IV: SAR of 1-[2-thiazol-5-yl-(2-aminoethyl)]-4-n-propylpiperazine derivatives

Frymarkiewicz¹,

Walczyński²

2009

European Journal of Medicinal Chemistry

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Section: Introductionsupporting

confidence: 56%

Non-imidazole histamine H3 ligands, Part IV: SAR of 1-[2-thiazol-5-yl-(2-aminoethyl)]-4-n-propylpiperazine derivatives

Frymarkiewicz¹,

Walczyński²

2009

European Journal of Medicinal Chemistry

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“…Heterocyclic compounds are widely distributed in nature. Many of them show drug active properties have increased the importance of such biological activities such as antimalarial [7], antibacterial [8], antifungal [9], antidepressant [10,11], anticonvulsant [12,13], antiinflammatory [14], antidiabetic [15], antiviral [16], antihistamine [17], anticarcinogen and antioxidant [18]. For example, quinine was isolated from the bark of Cinchona trees and has been used for the treatment of malaria [19].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Thiazole Compounds in the Presence of Various Reagents, Catalysts and Solvents

Berber

2022

Sakarya University Journal of Science

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The reaction medium plays a key role in organic synthesis and pharmaceutical research. There are many opinions on choosing the best condition, including cost and environmental implications, but the main requirement is that they have the necessary interaction with solvents to cause dissolution, precipitation, stabilization, or instability. For this purpose, in this article synthesis of the thiazole ring was made under various reaction conditions. So new compounds 2-(isoquinolin-5-ylimino)-3-phenylthiazolidin-4-one (1), (4-amino-3-phenylthiazol-2(3H)-ylidene) isoquinolin-5-amine (2), (4-amino-3-phenylthiazol-2(3H)-ylidene) isoquinolin-5-amine (3) were synthesized from the reaction between thiourea derivative and monochloroacetic acid, diethyloxalate and chloro acetonitrile. For this synthesizes were created in various reaction conditions, using different bases (sodium acetate/sodyum etoksit/ triethylamine or pyridine) and solvents (1,4-dioxane, toluene, acetic acid, ethanol, tetrahydrofuran, dimethyl formamide). At the end of these reactions, the best efficiency was obtained with the one-pot reaction using THF/DMF, Et3N. The structures of all novel compounds reported herein were established using FT-IR, 1H NMR, and 13C NMR spectra as well as elemental analysis technique.

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“…Previously, our laboratory has described several non-imidazole piperazine-based histamine H 3 antagonists, consisting of 1-(2-thiazolobenzo)-, 1-(2-thiazolopyridine)- and 1-[2-thiazol-5-yl-(2-aminoethyl)] moieties with moderate to pronounced affinity for the receptor (Walczyński et al ., 1999, 2005; Frymarkiewicz and Walczynski, 2009). The SAR of 1-[(2-thiazolobenzo)-4- n -propyl]piperazines and 1-[(2-thiazolopyridine)-4- n -propyl]piperazines series, showed no significant difference in H 3 activities (Walczyński et al ., 1999, 2005).…”

Section: Introductionmentioning

confidence: 99%

“…The SAR of 1-[(2-thiazolobenzo)-4- n -propyl]piperazines and 1-[(2-thiazolopyridine)-4- n -propyl]piperazines series, showed no significant difference in H 3 activities (Walczyński et al ., 1999, 2005). These results prompted us to replace the benzo ring by 2-methyl-2-alkylaminoethyl amide, 2-methyl-2-alkylaminoethyl and 2-methyl-2-phenylalkylaminoethyl chains at position 5 of 1-(2-thiazol-5-yl)-4- n -propylpiperazine moiety.…”

Section: Introductionmentioning

confidence: 99%

Non-imidazole histamine H3 ligands: part V. synthesis and preliminary pharmacological investigation of 1-[2-thiazol-4-yl- and 1-[2-thiazol-5-yl-(2-aminoethyl)]-4-n-propylpiperazine derivatives

2012

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Series of 1-[2-thiazol-4-yl-(2-aminoethyl)]- and 1-[2-thiazol-5-yl-(2-aminoethyl)]-4-n-propylpiperazine derivatives have been prepared and in vitro tested as H3-receptor antagonists (the electrically evoked contraction of the guinea-pig jejunum). It appeared that by comparison of homologous pairs, the 1-[2-thiazol-5-yl-(2-aminoethyl)]-4-n-propylpiperazines (3a,b and 4a–d) have much higher potency than their analogous 1-[2-thiazol-4-yl-(2-aminoethyl)]-4-n-propylpiperazines (2a–k). Based on the obtained results, we observed the 5-position of 2-methyl-2-R-aminoethyl substituents in the thiazole ring is favourable for histamine H3 receptor antagonist activity, whereas its presence in position 4 leads, almost in each case, to strong decrease of activity.

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Non-Imidazole Histamine H3 Ligands, Part 2: New 2-Substituted Benzothiazoles as Histamine H3 Antagonists

Cited by 31 publications

References 22 publications

Non-imidazole histamine H3 ligands, Part IV: SAR of 1-[2-thiazol-5-yl-(2-aminoethyl)]-4-n-propylpiperazine derivatives

Non-imidazole histamine H3 ligands, Part IV: SAR of 1-[2-thiazol-5-yl-(2-aminoethyl)]-4-n-propylpiperazine derivatives

Synthesis and Characterization of Thiazole Compounds in the Presence of Various Reagents, Catalysts and Solvents

Non-imidazole histamine H3 ligands: part V. synthesis and preliminary pharmacological investigation of 1-[2-thiazol-4-yl- and 1-[2-thiazol-5-yl-(2-aminoethyl)]-4-n-propylpiperazine derivatives

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