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【结 构 式】

【药物名称】(-)-(S)-Bromofosfamide, CBM-11

【化学名称】3-(2-Bromoethyl)-N-(2-chloroethyl)-2H-tetrahydro-1,3,2-oxazaphosphorin-2-amine 2-oxide

【CA登记号】146452-37-1

【 分 子 式 】C7H15BrClN2O2P

【 分 子 量 】305.5406

【开发单位】Polish Academy of Science (Originator)

【药理作用】Lung Cancer Therapy, Non-Small Cell Lung Cancer Therapy, Oncolytic Drugs, DNA Alkylating Drugs

合成路线1

Condensation of the chiral 2-chloro-3-(alpha-methylbenzyl)tetrahydro-2H-1,3,2-oxaazaphosphorine 2-oxide (I) with 2-chloroethylamine (II) afforded the 2-(chloroethylamino) derivative (III). The chiral auxiliary group of (III) was then removed by catalytic hydrogenation with H2 over -Pd/C yielding (R)-2-(2-chloroethylamino)tetrahydro-2H-1,3,2-oxaazaphosphorine 2-oxide (IV). Acylation of (IV) with bromoacetyl bromide (V) in the presence of triethylamine hydrobromide furnished bromoacetamide (VI). The amide carbonyl group of (VI) was finally reduced by treatment with NaBH4 and BF3·Et2O.

1 Kinas, R.W.; Stec, W.J.; Kusnierczyk, H.; Misiura, K.; radzikowski, C.; (S)-(-)-Bromofosfamide (CBM-11): Synthesis and antitumor activity and cytotoxicity in mice. Anti-Cancer Drugs 2001, 12, 5, 453.
2 Kutner, A.; Grynkiewicz, G.; Stec, W.J.; Radzikowski, C.; Szelejeswki, W.; Kinas, R.; Misiura, K.; Grodner, J.; Kusnierczyk, H.; Pilichowska, S.; Process for the production of the derivs. of 1,3,2-oxazaphosphorinane. EP 0295576 .
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) 56222 2-chloro-3-[(1S)-1-phenylethyl]-1,3,2lambda~5~-oxazaphosphinan-2-one C11H15ClNO2P 详情 详情
(II) 33455 2-chloro-1-ethanamine; 2-chloroethylamine C2H6ClN 详情 详情
(III) 56223 2-[(2-chloroethyl)amino]-3-[(1S)-1-phenylethyl]-1,3,2lambda~5~-oxazaphosphinan-2-one C13H20ClN2O2P 详情 详情
(IV) 56224 2-[(2-chloroethyl)amino]-1,3,2lambda~5~-oxazaphosphinan-2-one C5H12ClN2O2P 详情 详情
(V) 14005 2-Bromoacetyl bromide; Bromoacetyl bromide 598-21-0 C2H2Br2O 详情 详情
(VI) 56225 3-(2-bromoacetyl)-2-[(2-chloroethyl)amino]-1,3,2lambda~5~-oxazaphosphinan-2-one C7H13BrClN2O3P 详情 详情
Extended Information