QSAR study on H3-receptor affinity of benzothiazole derivatives of thioperamide was written by Bordi, Fabrizio;Mor, Marco;Morini, Giovanni;Plazzi, Pier Vincenzo;Silva, Claudia;Vitali, Tullo;Caretta, Antonio. And the article was included in Farmaco in 1994.Application In Synthesis of 6-Butoxybenzo[d]thiazol-2-amine The following contents are mentioned in the article:
Starting from the structure of thioperamide, a known H3-antagonist, a new series of compounds I (R = H, NO2, Br, etc.) with a benzothiazole nucleus instead of the cyclohexylcarbothioamide moiety was synthesized. Various substituents, selected by exptl. design, were introduced in position 6 of the benzothiazole nucleus, in order to change its physico-chem. characteristics. The lipophilicity of the synthesized compounds was measured by means of RP-HPLC, and their H3-receptor affinity was evaluated by competitive binding assays on rat cortex synaptosomes, with the labeled ligand Nα-[3H]methylhistamine. A QSAR anal. was performed on the exptl. data, using also substituent constants taken from the literature. The newly synthesized compounds showed lower H3-affinities than thioperamide; quant. structure-activity relationships, described by models obtained with PLS and MRS techniques, were observed among benzothiazole derivatives According to these relationships, any attempt to improve the potency of these compounds should involve the substitution of the benzothiazole moiety with less bulky and/or more flexible structures, which should also be less lipophilic and allow better electronic interactions with the binding site. 1-(Benzothiazol-2-yl)-4-[(1H)-imidazol-4-yl]piperidine represents a limit structure for H3-activity, since it seems impossible to improve its affinity by means of substitution in the studied position of the benzothiazole nucleus, as shown by predictions performed by a PLS model. This study involved multiple reactions and reactants, such as 6-Butoxybenzo[d]thiazol-2-amine (cas: 14372-65-7Application In Synthesis of 6-Butoxybenzo[d]thiazol-2-amine).
6-Butoxybenzo[d]thiazol-2-amine (cas: 14372-65-7) belongs to thiazole derivatives. Thiazole rings are planar and aromatic. Thiazoles are characterized by larger pi-electron delocalization than the corresponding oxazoles and have therefore greater aromaticity. Thiazole is a versatile building block for the construction and lead generation of new drug discoveries. Numerous diazole-based compounds are in clinical use as anticancer, antileukemic, antiinflammatory, antiviral, antifungal, antirheumatic, immunomodulator, and antiparasitic agents.Application In Synthesis of 6-Butoxybenzo[d]thiazol-2-amine
Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica