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【结 构 式】

【药物名称】

【化学名称】N-[2-(Dimethylamino)ethyl)-11-oxo-2-(3-pyridyl)-11H-pyrido[2,1-b]quinazoline-6-carboxamide

【CA登记号】

【 分 子 式 】C22H21N5O2

【 分 子 量 】387.44497

【开发单位】Wyeth Pharmaceuticals (Originator)

【药理作用】Oncolytic Drugs, DNA Topoisomerase II Inhibitors

合成路线1

Condensation of 2-amino-4-iodobenzoic acid (I) with 2-chloronicotinic acid (II) in refluxing EtOH in the presence of HCl yields pyridoquinazoline acid derivative (III), which is then condensed with N,N-dimethylethylenediamine (IV) in CH2Cl2 using BOP as coupling reagent to provide (V). Reaction of 2-bromopyridine (VI) in Et2O with n-BuLi and trimethylborate, followed by treatment with EtOH and HOAc, gives 3-pyridinyl boronic acid (VII), which is finally coupled to (V) in an Na2CO3 solution via a Suzuki coupling catalyzed by Pd(PPh3)4.

1 Kitchen, D.B.; Schow, S.R.; Casscles, W.T. Jr.; Discafani, C.; Trova, M.P.; Lassota, P.; Zhang, N.; Powell, D.W.; Hetero biarylpyridoquinazolinone derivatives as anticancer agents. 219th ACS Natl Meet (March 26 2000, San Francisco) 2000, Abst MEDI 59.
2 Trova, M.P.; Zhang, N. (American Cyanamid Co.); Hetero-biaryl-pyridoquinazolinone derivs. as anti-cancer agents. EP 0944628; WO 9823617 .
3 Trova, M.P.; Zhang, N. (American Cyanamid Co.); Hetero-biaryl-pyridoquinazolinone derivs. as anti-cancer agents. US 5908840 .
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) 19964 5-Iodoanthranilic acid; 2-amino-5-iodobenzoic acid 5326-47-6 C7H6INO2 详情 详情
(II) 28824 2-Chloropyridine-3-carboxylic acid; 2-Chloronicotinic acid 2942-59-8 C6H4ClNO2 详情 详情
(III) 42991 2-iodo-11-oxo-5,11-dihydro-10lambda(5)-pyrido[2,1-b]quinazoline-6-carboxylic acid C13H9IN2O3 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) 42992 N-[2-(dimethylamino)ethyl]-2-iodo-11-oxo-5,11-dihydro-10lambda(5)-pyrido[2,1-b]quinazoline-6-carboxamide C17H19IN4O2 详情 详情
(VI) 13265 3-Bromopyridine 626-55-1 C5H4BrN 详情 详情
(VII) 38825 3-pyridinylboronic acid 1692-25-7 C5H6BNO2 详情 详情
Extended Information