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  • Synthesis and anti-inflammatory effects of new piperazine and ethanolamine derivatives of H(1)-antihistaminic drugs.

Synthesis and anti-inflammatory effects of new piperazine and ethanolamine derivatives of H(1)-antihistaminic drugs.

Mini reviews in medicinal chemistry (2012-08-11)
Abbas Ahmadi, Mohsen Khalili, Ali Nafarie, Arash Yazdani, Babak Nahri-Niknafs
ZUSAMMENFASSUNG

In addition to their antihistamine effects, H1-receptor antagonists possess pharmacological properties that are not uniformly distributed among this class of drugs, such as anti-inflammatory, anti-allergic and antiplatelet activities. In this paper, Cyclizine (1-benzhydryl-4-methyl-piperazine, I), bromodiphenhydramine (2-[(4-bromophenyl)-phenylmethoxy]-N, N-dimethylethanamine, II) and some of their new piperazine and ethanolamine derivatives (III-VIII) inducing changes in substitution of phenyl and amine moieties were synthesized and their acute and chronic antiinflammatory effects were evaluated by standard pharmacological tests. The results showed that substitution of phenyl by tolyl, anisol and cumene groups in piperazine family could remarkably decrease acute inflammation in these new drugs. Also, substitution of dimethylamine by morpholine group could not decrease this inflammation in new synthesized ethanolamine family. But the results from the cotton pellet-induced granuloma formation in rats showed that none of drugs (I-VIII) were effective to reduce the chronic inflammation.

MATERIALIEN
Produktnummer
Marke
Produktbeschreibung

Sigma-Aldrich
Ethanolamin, ≥99%
Sigma-Aldrich
Ethanolamin, ≥98%
Sigma-Aldrich
Ethanolamin, purified by redistillation, ≥99.5%
Sigma-Aldrich
Piperazin, ReagentPlus®, 99%
Sigma-Aldrich
Ethanolamin, ACS reagent, ≥99.0%
Sigma-Aldrich
Diphenhydramin -hydrochlorid, ≥98% (HPLC)
Supelco
Diphenhydramin -hydrochlorid, Pharmaceutical Secondary Standard; Certified Reference Material
Sigma-Aldrich
Piperazin, BioUltra, anhydrous, ≥99.0% (T)
Sigma-Aldrich
Ethanolamin, liquid, BioReagent, suitable for cell culture, ≥98%
Supelco
Piperazin Hexahydrat, analytical standard
Sigma-Aldrich
Ethanolamin, puriss. p.a., ACS reagent, ≥99.0% (GC/NT)
Supelco
Ethanolamin, analytical standard
Supelco
Diphenhydramine hydrochloride solution, 1.0 mg/mL in methanol (as free base), ampule of 1 mL, certified reference material, Cerilliant®
Diphenhydramin -hydrochlorid, European Pharmacopoeia (EP) Reference Standard