CAS: 86357-09-7; 2-Amino-9-((2,3-Dihydroxypropoxy)Methyl)-1,9-Dihydro-6H-Purin-6-One
该化合物是一种合成抗病毒化合物,在结构上与甘氏洛维病毒感染有关,主要用于治疗cytomegalo病毒(CMV)感染;Iso Ganciclovir具有类似的药理特性,作为干扰病毒DNA合成的核素类比,其作用机制包括抑制病毒DNA聚合酶,从而防止病毒遗传材料的复制;该化合物的特点是能够有选择地瞄准受感染细胞,从而提高其治疗效力,同时尽量减少对未感染细胞的毒性;Iso Ganciclovir通常在临床环境中进行治疗,其效力经常在病毒抗药性和病人反应背景下进行评估;与许多抗病毒剂一样,潜在副作用可能包括血液毒性和其他系统反应;继续研究其在病毒学中的全部潜力和应用,特别是在抗病毒菌株方面.
- 英文名称2-Amino-9-((2,3-Dihydroxypropoxy)Methyl)-1,9-Dihydro-6H-Purin-6-One
- 中文名称异更昔洛韦
- IUPAC名称2-amino-9-((2,3-dihydroxypropoxy)methyl)-1,9-dihydro-6H-purin-6-one
- 其它别名Ganciclovir Related Compound A (15 Mg) ((Rs)-2-Amino-9-(2,3-Dihydroxy-Propoxymethyl)-1,9-Dihydro-Purin-6-One); 2-Amino-9-[(2,3-Dihydroxypropoxy)Methyl]-1,9-Dihydro-6H-Purin-6-One; 2-Amino-9-(2,3-Dihydroxypropoxymethyl)-3H-Purin-6-One; Ganciclovir Ep Impurity E; Gancyclovir Impurity 9; Ganciclovir Impurity 5(Ganciclovir Ep Impurity E); Iso Ganciclovir; Ganciclovir Ep Impurity E (Iso-Ganciclovir)
- CAS编号86357-09-7
- MFCD编号:MFCD27977948
- EINECS号:112-518-5
- FDA UNII编号:NNJ00018WY
- 分子式:C9H13N5O4分子量:255.23
- 产品CID: 1864836
- 产品分类分析化学 → 标准品 → 药典标准品和杂质标准品
MSDS等安全信息
欧盟法规
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9-(2,3-diacetoxy-1-propoxymethyl)guanine 2-acetyl-9-guanine(+/-)-N2-acetyl-9-(2,3-diacetoxy-1-propoxy)methylguanine 2,9-diacetylguanine 2,6,9-tris(trimethylsilyl)guanine合成工艺路线路线简述
- 1429306-12-6 = 86357-09-7
反应条件:1.1 Catalysts: Palladium Solvents: Methanol
标题:Synthesis Of Valganciclovir Hydrochloride Congeners
作者:Babu,K. Srihari; Et Al
参考文献:Synthetic Communications 日期:2013 卷标:43(13) 页码:1751-1758]
1429306-11-5 = 86357-09-7
反应条件:1.1 Reagents: Permanganic Acid (Hmno4),Potassium Salt (1:1) Solvents: Acetone,Water2.1 Catalysts: Palladium Solvents: Methanol
标题:Synthesis Of Valganciclovir Hydrochloride Congeners
作者:Babu,K. Srihari; Et Al
参考文献:Synthetic Communications 日期:2013 卷标:43(13) 页码:1751-1758]
3056-33-5 + 86357-10-0 = 86357-09-7
反应条件:1.1 Reagents: Ethanesulfonic Acid2.1 Reagents: Methylamine
标题:Synthesis And Antiherpetic Activity Of (S)-,(R)-,And (+/-)-9-[(2,3-Dihydroxy-1-Propoxy)Methyl]Guanine,Linear Isomers Of 2'-Nor-2'-Deoxyguanosine
作者:Ashton,Wallace T.; Et Al
参考文献:Journal Of Medicinal Chemistry 日期:1985 卷标:28(7) 页码:926-33]
19916-73-5 + 3970-20-5 = 86357-09-7
反应条件:1.1 Reagents: Sodium Hydride Solvents: Dimethylformamide2.1 Reagents: Permanganic Acid (Hmno4),Potassium Salt (1:1) Solvents: Acetone,Water3.1 Catalysts: Palladium Solvents: Methanol
标题:Synthesis Of Valganciclovir Hydrochloride Congeners
作者:Babu,K. Srihari; Et Al
参考文献:Synthetic Communications 日期:2013 卷标:43(13) 页码:1751-1758]
3376-59-8 = 86357-09-7 + 82410-32-0
反应条件:1.1 Reagents: Hydrochloric Acid Solvents: 1,2-Dichloroethane2.1 Reagents: Hexamethyldisilazane,Ammonium Sulfate2.2 Reagents: Tetrabutylammonium Iodide Solvents: 1,2-Dichloroethane3.1 Reagents: Sodium Hydroxide Solvents: Water
标题:Acyclic Nucleosides Containing Two Heterocyclic Bases
作者:Ogilvie,Kelvin K.; Et Al
参考文献:Nucleosides & Nucleotides 日期:1986 卷标:5(2) 页码:169-83]
= 86357-09-7
反应条件:1.1 Reagents: Hydrochloric Acid Solvents: Methanol,Water; 3 H,25 - 30 °C1.2 Reagents: Ammonia Solvents: Methanol,Water; 20 H,25 - 30 °C
标题:An Alternative Approach To Isoganciclovir: A Prominent Impurity In The Antiviral Drug Ganciclovir
作者:Sundaram,Dhanraj T. S. S.; Et Al
参考文献:Scientia Pharmaceutica 日期:2015 卷标:83(2) 页码:233-241]
86357-11-1 = 86357-09-7
反应条件:1.1 Reagents: Methylamine
标题:Synthesis And Antiherpetic Activity Of (S)-,(R)-,And (+/-)-9-[(2,3-Dihydroxy-1-Propoxy)Methyl]Guanine,Linear Isomers Of 2'-Nor-2'-Deoxyguanosine
作者:Ashton,Wallace T.; Et Al
参考文献:Journal Of Medicinal Chemistry 日期:1985 卷标:28(7) 页码:926-33]
1807753-76-9 + 3056-33-5 + 1807753-77-0 = 86357-09-7
反应条件:1.1 Catalysts: P-Toluenesulfonic Acid Solvents: Dimethylformamide; 6 H,110 °C2.1 Reagents: Hydrochloric Acid Solvents: Methanol,Water; 3 H,25 - 30 °C2.2 Reagents: Ammonia Solvents: Methanol,Water; 20 H,25 - 30 °C
标题:An Alternative Approach To Isoganciclovir: A Prominent Impurity In The Antiviral Drug Ganciclovir
作者:Sundaram,Dhanraj T. S. S.; Et Al
参考文献:Scientia Pharmaceutica 日期:2015 卷标:83(2) 页码:233-241]
4740-78-7 + 5464-28-8 = 86357-09-7
反应条件:1.1 Reagents: Zinc Chloride Solvents: Acetic Acid2.1 Reagents: Ethanesulfonic Acid3.1 Reagents: Methylamine
标题:Synthesis And Antiherpetic Activity Of (S)-,(R)-,And (+/-)-9-[(2,3-Dihydroxy-1-Propoxy)Methyl]Guanine,Linear Isomers Of 2'-Nor-2'-Deoxyguanosine
作者:Ashton,Wallace T.; Et Al
参考文献:Journal Of Medicinal Chemistry 日期:1985 卷标:28(7) 页码:926-33]
4167-35-5 + 4382-76-7 = 86357-09-7
反应条件:1.1 Catalysts: P-Toluenesulfonic Acid Solvents: Hexane; 2 H,-10 °C2.1 Catalysts: P-Toluenesulfonic Acid Solvents: Dimethylformamide; 6 H,110 °C3.1 Reagents: Hydrochloric Acid Solvents: Methanol,Water; 3 H,25 - 30 °C3.2 Reagents: Ammonia Solvents: Methanol,Water; 20 H,25 - 30 °C
标题:An Alternative Approach To Isoganciclovir: A Prominent Impurity In The Antiviral Drug Ganciclovir
作者:Sundaram,Dhanraj T. S. S.; Et Al
参考文献:Scientia Pharmaceutica 日期:2015 卷标:83(2) 页码:233-241]
= 86357-09-7
反应条件:1.1 Reagents: Hydrochloric Acid2.1 Reagents: Sodium Hydride Solvents: Dimethylformamide3.1 Reagents: Permanganic Acid (Hmno4),Potassium Salt (1:1) Solvents: Acetone,Water4.1 Catalysts: Palladium Solvents: Methanol
标题:Synthesis Of Valganciclovir Hydrochloride Congeners
作者:Babu,K. Srihari; Et Al
参考文献:Synthetic Communications 日期:2013 卷标:43(13) 页码:1751-1758]
56-81-5 = 86357-09-7
反应条件:1.1 Catalysts: Sulfuric Acid Solvents: Hexane2.1 Catalysts: P-Toluenesulfonic Acid Solvents: Hexane; 6 H,60 °C3.1 Catalysts: P-Toluenesulfonic Acid Solvents: Dimethylformamide; 6 H,110 °C4.1 Reagents: Hydrochloric Acid Solvents: Methanol,Water; 3 H,25 - 30 °C4.2 Reagents: Ammonia Solvents: Methanol,Water; 20 H,25 - 30 °C
标题:An Alternative Approach To Isoganciclovir: A Prominent Impurity In The Antiviral Drug Ganciclovir
作者:Sundaram,Dhanraj T. S. S.; Et Al
参考文献:Scientia Pharmaceutica 日期:2015 卷标:83(2) 页码:233-241]
= 86357-09-7 + 82410-32-0
反应条件:1.1 Reagents: Sodium Hydroxide Solvents: Water
标题:Acyclic Nucleosides Containing Two Heterocyclic Bases
作者:Ogilvie,Kelvin K.; Et Al
参考文献:Nucleosides & Nucleotides 日期:1986 卷标:5(2) 页码:169-83]
10310-21-1 = 86357-09-7 + 82410-32-0
反应条件:1.1 Reagents: Hexamethyldisilazane,Ammonium Sulfate1.2 Reagents: Tetrabutylammonium Iodide Solvents: 1,2-Dichloroethane2.1 Reagents: Sodium Hydroxide Solvents: Water
标题:Acyclic Nucleosides Containing Two Heterocyclic Bases
作者:Ogilvie,Kelvin K.; Et Al
参考文献:Nucleosides & Nucleotides 日期:1986 卷标:5(2) 页码:169-83
📜O-6-苄基鸟嘌呤置于potassium Permanganate,Palladium 10% On Activated Carbon,Sodium Hydride体系中,用 甲醇,N,N-二甲基甲酰胺,丙酮 作为反应溶剂,化学反应生成 异更昔洛韦
参考文献:盐酸缬更昔洛韦同系物的合成
标题:盐酸缬更昔洛韦同系物的合成
摘要:摘要 盐酸缬更昔洛韦 (1) 用于治疗免疫系统较弱患者的巨细胞病毒 (Cmv) 视网膜炎.盐酸缬更昔洛韦是更昔洛韦 (2) 的 L-缬氨酰酯的盐酸盐,以两种非对映异构体的混合物形式存在.根据美国食品和药物管理局的规范,盐酸缬更昔洛韦1的非对映体比例应保持在55:45至45:55的范围内.根据美国食品和药物管理局的规范,盐酸缬更昔洛韦1的非对映体比例应保持在55:45至45:55的范围内.在盐酸缬更昔洛韦的工艺开发过程中,除了最终的活性药物成分外,还观测到了六种相关物质(杂质).在这六种杂质中,更昔洛韦 (2) 和鸟嘌呤 (3) 分别是更昔洛韦的关键起始原料和降解杂质.其余四种杂质经鉴定为盐酸异缬更昔洛韦 (4),甲氧基甲基鸟嘌呤 (5),O-乙酰氧基更昔洛韦 (6) 和异戊酰更昔洛韦 (7).目前的工作描述了这四种杂质的合成和表征.图形概要
DOI:10.1080/00397911.2011.651249
海关参考信息
- 2905122000-异丙醇
2905310000-1,2-乙二醇
2905320000-1,2-丙二醇
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合成参考文献
参考文献:10.1056/nejm198603273141301
摘要:Collaborative DHPG Treatment Study Group. Treatment of serious cytomegalovirus infections with 9-(1,3-dihydroxy-2-propoxymethyl)guanine in patients with AIDS and other immunodeficiencies. N Engl J Med. 1986 Mar 27;314(13):801–5. doi: 10.1056/nejm198603273141301.
参考文献:10.1021/jm00155a015
摘要:Prisbe EJ, Martin JC, McGee DP, Barker MF, Smee DF, Duke AE, Matthews TR, Verheyden JP. Synthesis and antiherpes virus activity of phosphate and phosphonate derivatives of 9-[(1,3-dihydroxy-2-propoxy)methyl]guanine. J Med Chem. 1986 May;29(5):671–5. doi: 10.1021/jm00155a015.
参考文献:10.1021/jm00155a039
摘要:Karkas JD, Ashton WT, Canning LF, Liou R, Germershausen J, Bostedor R, Arison B, Field AK, Tolman RL. Enzymatic phosphorylation of the antiherpetic agent 9-[(2,3-dihydroxy-1-propoxy)methyl]guanine. J Med Chem. 1986 May;29(5):842–8. doi: 10.1021/jm00155a039.
参考文献:10.1128/aac.28.2.172
摘要:Shanley JD, Morningstar J, Jordan MC. Inhibition of murine cytomegalovirus lung infection and interstitial pneumonitis by acyclovir and 9-(1,3-dihydroxy-2-propoxymethyl)guanine. Antimicrob Agents Chemother. 1985 Aug;28(2):172–5.
参考文献:10.1128/aac.28.2.240
摘要:Freitas VR, Smee DF, Chernow M, Boehme R, Matthews TR. Activity of 9-(1,3-dihydroxy-2-propoxymethyl)guanine compared with that of acyclovir against human, monkey, and rodent cytomegaloviruses. Antimicrob Agents Chemother. 1985 Aug;28(2):240–5.
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