6,8,11-trihydroxy-7H-benzo[e]perimidin-7-one -Drug Synthesis Database

【结构式】

【分子编号】42952

【品名】6,8,11-trihydroxy-7H-benzo[e]perimidin-7-one

【CA登记号】

【分子式】C₁₅H₈N₂O₄

【分子量】280.2396

【元素组成】C 64.29% H 2.88% N 10% O 22.84%

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：(VIII)

The cyclization of anthracenedione derivative (I) with formamide in refluxing dimethylacetamide (DMA) in the presence of NH4VO3 affords benzo[e]perimidinone derivative (II), whose benzyl groups are removed with TFA to yield (III). Intermediate (III) is finally heated with 2-(dimethylamino)ethylamine (IV) in N,N,N',N'-tetramethylethylenediamine and a small amount of water. Alternatively, the target product can be obtained as follows: Reduction of the nitro group of anthracenedione derivative (V) by means of hydrazine and Pd/C provides amine (VI), which is then cyclized with formamide in phenol to give (VII). The removal of the benzyl groups of (VII) by treatment with TFA yields intermediate (VIII), which is finally condensed with 2-(dimethylamino)ethylamine (IV) under similar conditions as described for (III).

参考文献中间体

合成目标

【1】 Stefanska, B.; Bontemps-Gracz, M.M.; Dzieduszycka, M.; Borowski, E.; 8,11-Dihydroxy-6-[8aminoalkyl)amino]-7H-benzo[e]perimidin-7-ones with activity in multidrug-resistant cell lines: Synthesis and antitumor evaluation. J Med Chem 1999, 42, 18, 3494.
【2】 Borowski, E. (Politechnika Gdanska); New derivs. of 6-[(aminoalkyl)amino]-7H-benzo[e]-perimidin-7-one, method of their preparation, and their use as a medicament. WO 9825910 .

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)	42946	1,4-diamino-5,8-bis(benzyloxy)anthra-9,10-quinone		C₂₈H₂₂N₂O₄	详情	详情
(II)	42947	6-amino-8,11-bis(benzyloxy)-7H-benzo[e]perimidin-7-one		C₂₉H₂₁N₃O₃	详情	详情
(III)	42948	6-amino-8,11-dihydroxy-7H-benzo[e]perimidin-7-one		C₁₅H₉N₃O₃	详情	详情
(IV)	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
(V)	42949	1,4-bis(benzyloxy)-5-hydroxy-8-nitroanthra-9,10-quinone		C₂₈H₁₉NO₇	详情	详情
(VI)	42950	1-amino-5,8-bis(benzyloxy)-4-hydroxyanthra-9,10-quinone		C₂₈H₂₁NO₅	详情	详情
(VII)	42951	8,11-bis(benzyloxy)-6-hydroxy-7H-benzo[e]perimidin-7-one		C₂₉H₂₀N₂O₄	详情	详情
(VIII)	42952	6,8,11-trihydroxy-7H-benzo[e]perimidin-7-one		C₁₅H₈N₂O₄	详情	详情

合成路线2

该中间体在本合成路线中的序号：(IV)

Isoniazid (I) was treated with carbon disulfide and KOH to give potassium 4-pyridyl dithiocarbazinate (II). Cyclization of (II) in the presence of hydrazine produced the amino triazole (III). This was condensed with 5-bromoisatin (IV), yielding the imino adduct (V). Finally, Mannich reaction of (V) with piperidine (VI) and formaldehyde furnished the title compound.

参考文献中间体

合成目标

【1】 de Clercq, E.; Nath, G.; Pandeya, S.N.; Sriram, D.; Synthesis, antibacterial, antifungal and anti-HIV evaluation of Schiff and Mannich bases of isatin and its derivatives with triazole. Arzneim-Forsch Drug Res 2000, 50, 1, 55.

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)	26079	Isonicotinohydrazide	54-85-3	C₆H₇N₃O	详情	详情
(II)	43763	potassium 2-isonicotinoyl-1-hydrazinecarbodithioate		C₇H₆KN₃OS₂	详情	详情
(III)	43764	4-amino-5-(4-pyridinyl)-4H-1,2,4-triazole-3-thiol; 4-amino-5-(4-pyridinyl)-4H-1,2,4-triazol-3-ylhydrosulfide		C₇H₇N₅S	详情	详情
(IV)	42952	6,8,11-trihydroxy-7H-benzo[e]perimidin-7-one		C₁₅H₈N₂O₄	详情	详情
(V)	43765	5-bromo-3-[[3-(4-pyridinyl)-5-sulfanyl-4H-1,2,4-triazol-4-yl]imino]-1H-indol-2-one		C₁₅H₉BrN₆OS	详情	详情
(VI)	10158	Piperidine	110-89-4	C₅H₁₁N	详情	详情

Extended Information