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【结 构 式】

【药物名称】NND, CD-349

【化学名称】3-(2-Nitrooxypropyl) 5-(3-nitrooxypropyl) 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

【CA登记号】88594-08-5

【 分 子 式 】C21H24N4O12

【 分 子 量 】524.44503

【开发单位】Taisho (Originator)

【药理作用】Asthma Therapy, Bronchodilators, CARDIOVASCULAR DRUGS, Hypertension, Treatment of, RESPIRATORY DRUGS, Calcium Channel Blockers

合成路线1

By cyclization of 3-nitrobenzaldehyde (I) with 3-nitratopropyl-3-aminocrotonate (II) and 2-nitratopropyl acetoacetate (III) in refluxing benzene. The starting products (II) and (III) are obtained as follows: The reaction of diketene (IV) with 3-bromopropanol (V) by means of sodium acetate at 50 C gives 3-bromopropyl acetoacetate (VI), which by reaction with AgNO3 in refluxing acetonitrile is converted to 3-nitratopropyl acetoacetate (VII). Finally, this compound is treated with NH3 in THF to afford the aminocrotonic ester (II). The reaction of diketene (IV) with 2-chloropropanol (VIII) as before gives 2-chloropropyl acetoacetate (IX), which is treated with AgNO3 as before to yield acetoacetate (III).

1 Hatayama, K.; Sawada, J.; Nakazato, A.; Ogawa, T.; Ito, S. (Taisho Pharmaceutical Co., Ltd.); 1,4-Dihydropyridine derivs.. EP 0092936; US 4472411 .
2 Prous, J.; Castaner, J.; CD-349. Drugs Fut 1988, 13, 7, 610.
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) 12646 3-Nitrobenzaldehyde 99-61-6 C7H5NO3 详情 详情
(II) 13999 3-(nitrooxy)propyl (E)-3-amino-2-butenoate C7H12N2O5 详情 详情
(III) 22628 2-(nitrooxy)propyl 3-oxobutanoate C7H11NO6 详情 详情
(IV) 21896 4-methyl-2H-oxet-2-one C4H4O2 详情 详情
(V) 12573 3-Bromo-1-propanol; 3-Bromopropanol 627-18-9 C3H7BrO 详情 详情
(VI) 22631 3-bromopropyl 3-oxobutanoate C7H11BrO3 详情 详情
(VII) 22632 3-(nitrooxy)propyl 3-oxobutanoate C7H11NO6 详情 详情
(VIII) 22633 2-chloro-1-propanol 78-89-7 C3H7ClO 详情 详情
(IX) 22634 2-chloropropyl 3-oxobutanoate C7H11ClO3 详情 详情
Extended Information