(2S,3S)-3-azido-1,2,4-butanetriol | 136599-19-4

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: (2S,3S)-3-azido-1,2,4-butanetriol
• 英文别名: (2S,3S)-3-azidobutane-1,2,4-triol；3-azido-3-deoxy-L-erythritol；3-azido-butane-1,2,4-triol
• CAS: 136599-19-4
• 化学式: C₄H₉N₃O₃
• 分子量: 147.134
• InChiKey: WTDMEGHZIYGENC-IUYQGCFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  75
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3S)-3-azido-1,2,4-butanetriol 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 生成 L-erythro-3-amino-butane-1,2,4-triol
  参考文献：
  名称：

  Process for Preparing 5,7 Diaminopyrazolo [1,5-a] Pyrimidine Compounds

  摘要：

  制备特定5,7-二氨基吡唑并[1,5-α]嘧啶化合物的方法包括在溶剂体系中将一种初级或次级胺和受保护的5-卤代-7-氨基吡唑并[1,5-α]嘧啶化合物反应，所述溶剂体系包括水和一个或多个有机溶剂，可选地在外源碱的存在下。

  公开号：

  US20120041198A1
• 作为产物：
  描述：

  1-[(1R,2S)-3-ethoxy-1-(ethoxycarbonyl)-2-hydroxy-3-oxopropyl]-1,2-triazadien-2-ium 在 sodium tetrahydroborate 、 lithium chloride 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 (2S,3S)-3-azido-1,2,4-butanetriol
  参考文献：
  名称：

  脯氨酸催化反应合成氮杂糖

  摘要：

  我们报道了从对映体纯的l-和d-酒石酸二乙酯中获得氮杂糖的有效途径。关键步骤是脯氨酸催化的醛醇缩合，其中脯氨酸的两种对映异构体均已用作催化剂，从而提供了互补的抗醛醇缩合物。

  DOI：

  10.1021/jo060568b

文献信息

• [EN] ASPARTYL PROTEASE INHIBITORS<br/>[FR] INHIBITEURS D'ASPARTYL PROTÉASE
  申请人：MEDIVIR AB

  公开号：WO2010107384A1

  公开（公告）日：2010-09-23

  A compound of formula (I) N-oxides, addition salts, quaternary amines metal complexes stereochemically isomeric forms and metabolites thereof, wherein A is CR1 Or N; formula (A) or formula (B) D is H, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, G is NR10 or O Q is C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6Cycloalkyl, aryl or heterocyclyl; W is H, C1-C6alkyl, C3-C6Cycloalkyl, CH2F, CHF2 or CF3; one of X' and X" is H or CH3, the other is C1-C3alkyl, F, OH, NRaRb, CF3 or N3; or X' and X" are both F; Y is NRd or O; Z is O, NRa, CHRd, CF2 or S(=0)r or a bond; the other variables are as defined in the specification. The compounds of the invention are inhibitors of BACE and are among other things useful for the treatment and/or prevention of conditions associated with BACE activity such as Alzheimer's disease.

  公式（I）的化合物N-氧化物，加成盐，季铵盐金属配合物立体化异构体及其代谢物，其中A为CR1或N；公式（A）或公式（B）D为H，C1-C6烷基，C2-C6烯基，C2-C6炔基，G为NR10或O，Q为C1-C6烷基，C2-C6烯基，C2-C6炔基，C3-C6环烷基，芳基或杂环烷基；W为H，C1-C6烷基，C3-C6环烷基，CH2F，CHF2或CF3；X'和X"中的一个为H或CH3，另一个为C1-C3烷基，F，OH，NRaRb， 或N3；或者X'和X"都是F；Y为NRd或O；Z为O，NRa，CHRd，CF2或S（=0）r或键；其他变量如规范中定义。本发明的化合物是BACE的抑制剂，除其他用途外，还可用于治疗和/或预防与BACE活性相关的疾病，如阿尔茨海默病。
• Sphingolipid Synthesis via Olefin Cross Metathesis:  Preparation of a Differentially Protected Building Block and Application to the Synthesis of <scp>d</scp>-<i>e</i><i>rythro</i>-Ceramide
  作者：Anand Narain Rai、Amit Basu

  DOI：10.1021/ol049183a

  日期：2004.8.1

  The sphingolipid backbone is readily assembled by E-selective olefin cross metathesis of a suitable building block.

  鞘脂主链易于通过合适的结构单元的E-选择性烯烃交叉复分解而组装。
• Transition state analogue inhibitors of human methylthioadenosine phosphorylase and bacterial methylthioadenosine/S-adenosylhomocysteine nucleosidase incorporating acyclic ribooxacarbenium ion mimics
  作者：Keith Clinch、Gary B. Evans、Richard F.G. Fröhlich、Shivali A. Gulab、Jemy A. Gutierrez、Jennifer M. Mason、Vern L. Schramm、Peter C. Tyler、Anthony D. Woolhouse

  DOI：10.1016/j.bmc.2012.07.006

  日期：2012.9

  Several acyclic hydroxy-methylthio-amines with 3-5 carbon atoms were prepared and coupled via a methylene link to 9-deazaadenine. The products were tested for inhibition against human MTAP and Escherichia coli and Neisseria meningitidis MTANs and gave K-i values as low as 0.23 nM. These results were compared to those obtained with 1st and 2nd generation inhibitors (1S)-1-(9-deazaadenin-9-yl)-1,4-dideoxy-1,4-imino-5-methylthio-D-ribitol (MT-Immucillin-A, 3) and (3R,4S)-1-[9-deazaadenin-9-yl)methyl]3-hydroxy-4-methylthiomethylpyrrolidine (MT-DADMe-Immucillin-A, 4). The best inhibitors were found to exhibit binding affinities of approximately 2- to 4-fold those of 3 but were significantly weaker than 4. Cleavage of the 2,3 carbon-carbon bond in MT-Immucillin-A (3) gave an acyclic product (79) with a 21,500 fold loss of activity against E. coli MTAN. In another case, N-methylation of a side chain secondary amine resulted in a 250-fold loss of activity against the same enzyme [(+/-)-65 vs (+/-)-68]. The inhibition results were also contrasted with those acyclic derivatives previously prepared as inhibitors for a related enzyme, purine nucleoside phosphorylase (PNP), where some inhibitors in the latter case were found to be more potent than their cyclic counterparts. (C) 2012 Elsevier Ltd. All rights reserved.
• Mori, Kenji; Kinsho, Takeshi, Liebigs Annalen der Chemie, 1991, # 12, p. 1309 - 1316
  作者：Mori, Kenji、Kinsho, Takeshi

  DOI：——

  日期：——
• A Novel Pyrazolo[1,5-<i>a</i>]pyrimidine Is a Potent Inhibitor of Cyclin-Dependent Protein Kinases 1, 2, and 9, Which Demonstrates Antitumor Effects in Human Tumor Xenografts Following Oral Administration
  作者：Dean A. Heathcote、Hetal Patel、Sebastian H. B. Kroll、Pascale Hazel、Manikandan Periyasamy、Mary Alikian、Seshu K. Kanneganti、Ashutosh S. Jogalekar、Bodo Scheiper、Marion Barbazanges、Andreas Blum、Jan Brackow、Alekasandra Siwicka、Robert D. M. Pace、Matthew J. Fuchter、James P. Snyder、Dennis C. Liotta、Paul. S. Freemont、Eric O. Aboagye、R. Charles Coombes、Anthony G. M. Barrett、Simak Ali

  DOI：10.1021/jm100732t

  日期：2010.12.23

  Cyclin-dependent protein kinases (CDKs) are central to the appropriate regulation of cell proliferation, apoptosis, and gene expression. Abnormalities in CDK activity and regulation are common features of cancer, making CDK family members attractive targets for the development of anticancer drugs. Here, we report the identification of a pyrazolo[1,5-a]pyrimidine derived compound, 4k (BS-194), as a selective and potent CDK inhibitor, which inhibits CDK2, CDK1, CDK5, CDK7, and CDK9 (IC50 = 3, 30, 30, 250, and 90 nmol/L, respectively). Cell-based studies showed inhibition of the phosphorylation of CDK substrates, Rb and the RNA polymerase II C-terminal domain, down-regulation of cyclins A, E, and D1, and cell cycle block in the S and G(2)/M phases. Consistent with these findings, 4k demonstrated potent antiproliferative activity in 60 cancer cell lines tested (mean GI(50) = 280 nmol/L). Pharmacokinetic studies showed that 4k is orally bioavailable, with an elimination half-life of 178 min following oral dosing in mice. When administered at a concentration of 25 mg/kg orally, 4k inhibited human tumor xenografts and suppressed CDK substrate phosphorylation. These findings identify 4k as a novel, potent CDK selective inhibitor with potential for oral delivery in cancer patients.