69304-47-8
69304-47-8 結(jié)構(gòu)式
基本信息
溴夫啶
溴夫定
布里夫定
溴比夫定
布瑞夫定
溴乙烯尿苷
溴夫定/溴夫啶
溴夫定(標準品)
(E)-5-(2-溴乙烯基)-2'-脫氧核苷
BVDR
BrVDU
Helpin
Brivudin
SC-38394
BRIVUDINE
Brivudine BVdU
Brivudine USP/EP/BP
Bromovinyldeoxyuridine
物理化學性質(zhì)
制備方法
![(2E)-3-[1-(2-脫氧-BETA-D-赤式戊呋喃糖基)-1,2,3,4-四氫-2,4-二氧代-5-嘧啶基]-2-丙烯酸](/CAS/GIF/74131-06-9.gif)
74131-06-9
69304-47-8
一般步驟：向(E)-5-(2-羧基乙烯基)-1-(2-脫氧-β-D-赤式戊呋喃糖基)嘧啶-2,4(1H,3H)-二酮（5.777 g，19.37 mmol）的二甲基甲酰胺（29 mL）溶液中加入K2CO3（5.890 g，42.61 mmol），并將該懸浮液在室溫下攪拌15分鐘。在20℃下，于30分鐘內(nèi)滴加N-溴代琥珀酰亞胺（3.655 g，20.53 mmol）的溶液。反應完成后，過濾所得懸浮液，并用DMF洗滌固體。將合并的濾液和洗滌液在真空下蒸發(fā)至干，殘余物溶于甲醇中。向此溶液中加入硅膠，將懸浮液蒸發(fā)至干，然后將固體加載到色譜柱頂部。使用氯仿/甲醇（92:8，v/v）作為洗脫劑進行柱層析，得到白色固體（5.787 g，收率71.9%）。通過從水中重結(jié)晶得到白色粉末。產(chǎn)物的結(jié)構(gòu)通過1H-NMR和13C-NMR確認：1H-NMR (DMSO-d6; 300 MHz) δ 11.59 (1H, bs, NH-3), 8.08 (1H, s, H-6), 7.25 (1H, d, 3J = 13.6 Hz, H-5B), 6.85 (1H, d, J = 13.6 Hz, H-5A), 6.13 (1H, t, 3J = 6.5 Hz, H-1'), 5.29 (1H, bs, OH-3'), 5.13 (1H, bs, OH-5'), 4.24 (1H, m, H-3'), 3.79 (1H, m, H-4'), 3.66 (2H, m, H-5'), 2.51 (1H, m, H-2'), 2.14 (1H, m, H-2'); 13C-NMR (DMSO-d6; 75 MHz) δ 40.2 (C-2'), 61.3 (C-5'), 70.3 (C-4'), 84.8 (C-3'), 87.8 (C-1'), 108.9 (C-5B), 110.0 (C-5), 130.3 (C-5A), 149.6, 162.1 (C-2, C-4)。
參考文獻：
[1] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 24, p. 6663 - 6671
[2] RSC Advances, 2015, vol. 5, # 31, p. 24558 - 24563
[3] Patent: WO2005/12327, 2005, A2. Location in patent: Page/Page column 24-25
[4] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 20, p. 5640 - 5642
[5] Patent: US6653318, 2003, B1
| 報價日期 | 產(chǎn)品編號 | 產(chǎn)品名稱 | CAS號 | 包裝 | 價格 |
| 2025/05/22 | H27853 | (E)-5-(2-溴乙烯基)-2'-脫氧核苷, 98% (E)-5-(2-Bromovinyl)-2'-deoxyuridine, 98% | 69304-47-8 | 50mg | 634元 |
| 2025/05/22 | H27853 | (E)-5-(2-溴乙烯基)-2'-脫氧核苷, 98% (E)-5-(2-Bromovinyl)-2'-deoxyuridine, 98% | 69304-47-8 | 250mg | 1951元 |
| 2025/05/22 | H27853 | (E)-5-(2-溴乙烯基)-2'-脫氧核苷, 98% (E)-5-(2-Bromovinyl)-2'-deoxyuridine, 98% | 69304-47-8 | 1g | 5042元 |
常見問題列表
Brivudine is an analog of thymidine, and is incorporated into the viral DNA. It blocks the action of DNA polymerases, thus inhibiting viral replication. It has a stronger antiviral effect against the varicella-zoster virus compared with reference compounds such as aciclovir or penciclovir. It has high, selective activity against varicella zoster virus (VZV), inhibiting VZV replication, possibly through competitive inhibition of viral DNA polymerase, or by acting as an alternative substrate to deoxythymidine triphosphate, causing viral DNA strand breakage.
At a dose of 125 mg once daily, brivudine has proved to be superior to aciclovir with respect to reducing the period of new blister production, and has shortened the duration of post-herpetic neuralgia.