-Drug Synthesis Database

【结构式】

【药物名称】

【化学名称】5-[3-(Dimethylamino)propyl]-6-oxo-5,6-dihydrothieno[3',2':4,5]thieno[2,3-c]quinoline-9-carboxylic acid methyl ester hydrochloride

【CA登记号】

【分子式】C₂₀H₂₁ClN₂O₃S₂

【分子量】436.98297

【开发单位】Rudjer Boskovic Institute (Originator), University of Zagreb (Originator)

【药理作用】Oncolytic Drugs

合成路线1

Jones oxidation of 4-bromothiophene-2-carbaldehyde (I) leads to acid (II), which is further esterified with H2SO4/MeOH to furnish methyl 4-bromothiophene-2-carboxylate (III). Subsequent Heck coupling of aryl bromide (III) with cyclohexylammonium acrylate (IV) gives rise to the thienylacrylic acid (V). Cyclization of (V) with SOCl2 in the presence of pyridine produces the thienothiophene derivative (VI). Acid chloride (VI) is then coupled to N-(dimethylaminopropyl)aniline (VII) under Schotten-Baumann conditions, yielding amide (VIII). Finally, photochemical cyclization of (VIII) affords the target tetracyclic compound.

参考文献中间体

【1】 DoganKoruznjak, J.; Slade, N.; Zamola, B.; Pavelic, K.; Karminski-Zamola, G.; Synthesis, photochemical synthesis and antitumor evaluation of novel derivatives of thieno[3',2':4,5]thieno[2,3-c]quinolones. Chem Pharm Bull 2002, 50, 5, 656.

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)	24142	4-bromo-2-thiophenecarbaldehyde	18791-75-8	C₅H₃BrOS	详情	详情
(II)	64296	4-bromo-2-thiophenecarboxylic acid		C₅H₃BrO₂S	详情	详情
(III)	64297	methyl 4-bromo-2-thiophenecarboxylate		C₆H₅BrO₂S	详情	详情
(IV)	19139	acrylic acid	79-10-7	C₃H₄O₂	详情	详情
(V)	64298	(E)-3-[5-(methoxycarbonyl)-3-thienyl]-2-propenoic acid		C₉H₈O₄S	详情	详情
(VI)	64299	methyl 4-chloro-5-(chlorocarbonyl)thieno[2,3-b]thiophene-2-carboxylate		C₉H₄Cl₂O₃S₂	详情	详情
(VII)	64300	N-(3-anilinopropyl)-N,N-dimethylamine; N~1~,N~1~-dimethyl-N~3~-phenyl-1,3-propanediamine		C₁₁H₁₈N₂	详情	详情
(VIII)	64301	methyl 4-chloro-5-({[3-(dimethylamino)propyl]anilino}carbonyl)thieno[2,3-b]thiophene-2-carboxylate		C₂₀H₂₁ClN₂O₃S₂	详情	详情

Extended Information

Drug NewChemical Entity Original Patent(1)