1-chloro-4-nitro-9(10H)-acridinone -Drug Synthesis Database

【结构式】

【分子编号】52276

【品名】1-chloro-4-nitro-9(10H)-acridinone

【CA登记号】

【分子式】C₁₃H₇ClN₂O₃

【分子量】274.66296

【元素组成】C 56.85% H 2.57% Cl 12.91% N 10.2% O 17.48%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(IV)

2,6-Dichloro-3-nitrobenzoic acid (I) was condensed with aniline (II) to produce the anilinobenzoic acid (III), which was subsequently cyclized to the acridinone (IV) upon treatment with POCl3. Displacement of the chloride group of (IV) with 1,4-bis(3-aminopropyl)piperazine (V) in DMF afforded adduct (VI). The nitro group of (VI) was reduced by catalytic hydrogenation in the presence of Raney-Ni and formic acid, and the intermediate formamide was further cyclized under acidic conditions to the imidazoacridinone (VII). Finally, conversion of the primary amino group of (VII) to the target imide was achieved by heating with 3-nitro-1,8-naphthalenedicarboxylic anhydride (VIII) in DMF.

参考文献中间体

合成目标

【1】 Cholody, W.M.; Michejda, C.J.; Kosakowska-Cholody, T. (US Department of Health & Human Services); 1,8-Naphthalimide imidazo[4,5,1-de]acridones with anti-tumor activity. WO 0166545 .

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)	52274	2,5-Dichloro-3-nitrobenzoic acid	88-86-8	C₇H₃Cl₂NO₄	详情	详情
(II)	12294	Aniline; Phenylamine	62-53-3	C₆H₇N	详情	详情
(III)	52275	6-chloro-3-nitro-2-(phenylamino)benzoic acid		C₁₃H₉ClN₂O₄	详情	详情
(IV)	52276	1-chloro-4-nitro-9(10H)-acridinone		C₁₃H₇ClN₂O₃	详情	详情
(V)	52277	1,4-Bis(3-aminopropyl)piperazine; N,N'-Bis(3-Aminopropyl)piperazine; Bis aminopropyl piperazine; 1,4-Di(3-aminopropyl)piperazine	7209-38-3	C₁₀H₂₄N₄	详情	详情
(VI)	52278	1-({3-[4-(3-aminopropyl)-1-piperazinyl]propyl}amino)-4-nitro-9(10H)-acridinone		C₂₃H₃₀N₆O₃	详情	详情
(VII)	52279	5-({3-[4-(3-aminopropyl)-1-piperazinyl]propyl}amino)-6H-imidazo[4,5,1-de]acridin-6-one		C₂₄H₃₀N₆O	详情	详情
(VIII)	15864	5-nitro-1H,3H-benzo[de]isochromene-1,3-dione; 3-Nitro-1,8-naphthalic anhydride	3027-38-1	C₁₂H₅NO₅	详情	详情

合成路线2

该中间体在本合成路线中的序号：(I)

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