1-chloro-4-nitro-9-acridinamine; 1-chloro-4-nitro-9-acridinylamine -Drug Synthesis Database

【结构式】

【分子编号】63194

【品名】1-chloro-4-nitro-9-acridinamine; 1-chloro-4-nitro-9-acridinylamine

【CA登记号】

【分子式】C₁₃H₈ClN₃O₂

【分子量】273.67824

【元素组成】C 57.05% H 2.95% Cl 12.95% N 15.35% O 11.69%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(II)

1-Chloro-4-nitro-9,10-dihydroacridin-9-one (I) is refluxed with POCl3 in the presence of a catalytic amount of DMF and subsequently reacted with ammonium carbonate in hot phenol to provide the amino acridine (II). Displacement of the 4-chloro group of (II) with N,N-dimethylethanediamine (III) in DMF at 100 C leads to amine (IV). Cyclization of (IV) with SOCl2 yields the target thiadiazinoacridine, which is finally isolated as the corresponding maleate salt.

参考文献中间体

合成目标

【1】 Antonini, I.; Polucci, P.; Magnano, A.; Cacciamani, D.; Konieczny, M.T.; Paradziej-Lukowicz, J.; Martelli, S.; Rational design, synthesis and biological evaluation of thiadiazinoacridines: A new class of antitumor agents. Bioorg Med Chem 2003, 11, 3, 399.

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)	52276	1-chloro-4-nitro-9(10H)-acridinone		C₁₃H₇ClN₂O₃	详情	详情
(II)	63194	1-chloro-4-nitro-9-acridinamine; 1-chloro-4-nitro-9-acridinylamine		C₁₃H₈ClN₃O₂	详情	详情
(III)	14881	N-(2-aminoethyl)-N,N-dimethylamine; N(1),N(1)-dimethyl-1,2-ethanediamine; 2-Dimethylaminoethylamine	108-00-9	C₄H₁₂N₂	详情	详情
(IV)	63195	N-[2-(dimethylamino)ethyl]-N-(9-imino-4-nitro-9,10-dihydro-1-acridinyl)amine; N~1~-(9-imino-4-nitro-9,10-dihydro-1-acridinyl)-N~2~,N~2~-dimethyl-1,2-ethanediamine		C₁₇H₁₉N₅O₂	详情	详情

Extended Information