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【结 构 式】

【药物名称】GSQ-1530

【化学名称】N-[5-[N-[5-[N-[5-[N-(2-Amidinoethyl)carbamoyl]-1-methyl-1H-pyrrol-3-yl]carbamoyl]-1-methyl-1H-pyrrol-3-yl]carbamoyl]-1-methyl-1H-pyrrol-3-yl]-4,5-dichloroisothiazole-3-carboxamide acetate

【CA登记号】365211-22-9 (free base)

【 分 子 式 】C27H30Cl2N10O6S

【 分 子 量 】693.57355

【开发单位】GeneSoft (Originator)

【药理作用】Antibacterial Drugs, ANTIINFECTIVE THERAPY, Drugs Inhibiting Gene Expression

合成路线1

The condensation of 4-(tert-butoxycarbonylamino)-1-methyl-1H-pyrrole-2-carboxylic acid (I) with 4-amino-1-methyl-1H-pyrrole-2-carboxylic acid methyl ester (II) by means of DCC, HOBT and TEA in hot DMF gives the dimeric amide (III), which is hydrolyzed with NaOH in hot methanol/water to yield the carboxylic acid (IV). The condensation of (IV) with methyl ester (II) by means of HBTU and TEA in hot DMF affords the trimeric diamide (V), which is hydrolyzed with NaOH in methanol/water to provide the carboxylic acid (VI). The deprotection of the carbamate group of (VI) with HCl in ethyl acetate gives the trimeric amino acid (VII), which is condensed with 4,5-dichloroisothiazole-3-carboxylic acid (VIII) by means of HBTU and DIEA in DMF to yield the tetrameric carboxylic acid (IX). The condensation of (IX) with 3-aminopropionitrile (X) by means of HBTU and TEA in DMF affords the corresponding tetrameric tetraamide (XI), which is treated with gaseous HCl in methanol to provide the iminoester (XII). Finally, this compound is treated with NH3 in methanol to furnish the target carboxamidine.

1 Burli, R.; et al.; HARP: A novel class of antibiotics. 41st Intersci Conf Antimicrob Agents Chemother (Dec 16 2001, Chicago) 2001, Abst F-1685.
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) 53510 4-[(tert-butoxycarbonyl)amino]-1-methyl-1H-pyrrole-2-carboxylic acid 77716-11-1 C11H16N2O4 详情 详情
(II) 53511 methyl 4-amino-1-methyl-1H-pyrrole-2-carboxylate 180258-45-1 C7H10N2O2 详情 详情
(III) 53512 methyl 4-[({4-[(tert-butoxycarbonyl)amino]-1-methyl-1H-pyrrol-2-yl}carbonyl)amino]-1-methyl-1H-pyrrole-2-carboxylate n/a C18H24N4O5 详情 详情
(IV) 53513 4-[({4-[(tert-butoxycarbonyl)amino]-1-methyl-1H-pyrrol-2-yl}carbonyl)amino]-1-methyl-1H-pyrrole-2-carboxylic acid n/a C17H22N4O5 详情 详情
(V) 53514 methyl 4-[({4-[({4-[(tert-butoxycarbonyl)amino]-1-methyl-1H-pyrrol-2-yl}carbonyl)amino]-1-methyl-1H-pyrrol-2-yl}carbonyl)amino]-1-methyl-1H-pyrrole-2-carboxylate n/a C24H30N6O6 详情 详情
(VI) 53515 4-[({4-[({4-[(tert-butoxycarbonyl)amino]-1-methyl-1H-pyrrol-2-yl}carbonyl)amino]-1-methyl-1H-pyrrol-2-yl}carbonyl)amino]-1-methyl-1H-pyrrole-2-carboxylic acid n/a C23H28N6O6 详情 详情
(VII) 53516 4-{[(4-{[(4-amino-1-methyl-1H-pyrrol-2-yl)carbonyl]amino}-1-methyl-1H-pyrrol-2-yl)carbonyl]amino}-1-methyl-1H-pyrrole-2-carboxylic acid n/a C18H20N6O4 详情 详情
(VIII) 53517 4,5-Dichloroisothiazole-3-carboxylic acid 131947-13-2 C4HCl2NO2S 详情 详情
(IX) 53518 4-{[(4-{[(4-{[(4,5-dichloro-3-isothiazolyl)carbonyl]amino}-1-methyl-1H-pyrrol-2-yl)carbonyl]amino}-1-methyl-1H-pyrrol-2-yl)carbonyl]amino}-1-methyl-1H-pyrrole-2-carboxylic acid n/a C22H19Cl2N7O5S 详情 详情
(X) 38094 3-aminopropanenitrile 151-18-8 C3H6N2 详情 详情
(XI) 53519 4,5-dichloro-N-(5-{[(5-{[(5-{[(2-cyanoethyl)amino]carbonyl}-1-methyl-1H-pyrrol-3-yl)amino]carbonyl}-1-methyl-1H-pyrrol-3-yl)amino]carbonyl}-1-methyl-1H-pyrrol-3-yl)-3-isothiazolecarboxamide n/a C25H23Cl2N9O4S 详情 详情
(XII) 53520 methyl 3-{[(4-{[(4-{[(4-{[(4,5-dichloro-3-isothiazolyl)carbonyl]amino}-1-methyl-1H-pyrrol-2-yl)carbonyl]amino}-1-methyl-1H-pyrrol-2-yl)carbonyl]amino}-1-methyl-1H-pyrrol-2-yl)carbonyl]amino}propanimidoate n/a C26H27Cl2N9O5S 详情 详情
Extended Information