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SM ISO690:2012 BLAJA, Svetlana, LUNGU, Lidia, KUCHKOVA, Kaleria, CIOCARLAN, Alexandru, ARICU, Aculina. Synthesis of new molecular hybrids with phenothiazine fragment from norambreinolide. In: New frontiers in natural product chemistry, Ed. 7, 12-13 octombrie 2023, Chișinău. Chișinău, Republica Moldova: Tipografia "Artpoligraf", 2023, Ediția 7, p. 17. DOI: https://doi.org/10.19261/nfnpc.2023.ab10 |
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New frontiers in natural product chemistry Ediția 7, 2023 |
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Conferința " New frontiers in natural product chemistry." 7, Chișinău, Moldova, 12-13 octombrie 2023 | |||||||
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DOI:https://doi.org/10.19261/nfnpc.2023.ab10 | |||||||
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The known phenothiazine derivatives exhibit a wide spectrum of biological activities, including such as antiparasitic, antioxidant, anticancer, antiproliferative, antineoplastic, antimicrobial, etc. [1]. For this reason, terpeno-phenothiazine molecular hybrids represent one of the priority strategies of organic synthesis in the design of new bioactive compounds. Here are reported the results of the synthesis of new homodrimane hybrids with a phenothiazine fragment. Starting from (+)-sclareolide 1 the Δ8,13-bicyclohomofarnesoic acid 2 and 11-homodrim-6(8)-dien-12-oic acid 3 were synthesized in 6 and 5 steps in 62% and 81% overall yields, respectively [2,3]. Intermediate acyl chlorides 4 and 5 were generated in situ by treating acids 2 and 3 with oxalyl chloride in anhydrous benzene and then coupled with phenothiazine in the presence of triethylamine in methylene chloride on stirring to give hybrid phenothiazines 6 and 7 in depicted yields (see Scheme). The structures of all synthesized compounds were fully confirmed by spectral methods of analysis (IR, 1H, 13C and 15N NMR). |
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