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【结 构 式】

【药物名称】L-294, LASSBio-294

【化学名称】(E)-N'-(Thien-2-ylmethylene)-1,3-benzodioxole-5-carbohydrazide

【CA登记号】314021-07-3

【 分 子 式 】C13H10N2O3S

【 分 子 量 】274.30025

【开发单位】LASSBio (Originator), University of Maryland (Originator)

【药理作用】CARDIOVASCULAR DRUGS, Cerebrovascular Diseases, Treatment of, Heart Failure Therapy, NEUROLOGIC DRUGS, Positive Inotropic Agents, Phosphodiesterase III Inhibitors

合成路线1

Isosafrole (II) was obtained by isomerization of safrole (I) under basic conditions. Ozonolysis of (II), followed by reductive decomposition of the intermediate ozonide with Zn, furnished piperonal (III). Oxidation of aldehyde (III) with methanolic iodine produced the methyl ester (IV), which was converted to the corresponding hydrazide (V) upon treatment with hydrazine in refluxing EtOH. Finally, condensation of (V) with thiophene-2-carboxaldehyde (VI) yielded the title hydrazone.

1 Gonzalez-Serratos, H.; et al.; A novel thienylhydrazone, (2-thienylidene)3,4-methylenedioxybenzoylhydrazine, increases inotropism and decreases fatigue of skeletal muscle. J Pharmacol Exp Ther 2001, 299, 2, 588.
2 Sudo, R.T.; Alburquerque, E.X.; De Barreiro, E.J. (University of Maryland); Thienylhydrazon with digitalis-like properties (positive inotropic effects). WO 0078754 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 46334 5-allyl-1,3-benzodioxole C10H10O2 详情 详情
(II) 53072 5-[(E)-1-propenyl]-1,3-benzodioxole n/a C10H10O2 详情 详情
(III) 10127 1,3-Benzodioxole-5-carbaldehyde; Heliotropine 120-57-0 C8H6O3 详情 详情
(IV) 53073 methyl 1,3-benzodioxole-5-carboxylate n/a C9H8O4 详情 详情
(V) 53074 1,3-benzodioxole-5-carbohydrazide n/a C8H8N2O3 详情 详情
(VI) 30732 2-thiophenecarbaldehyde; Thiophene-2-carboxaldehyde 98-03-3 C5H4OS 详情 详情
Extended Information