(3S,4R)-吡咯烷-3,4-二醇 | 131565-87-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 中文名称: (3S,4R)-吡咯烷-3,4-二醇
• 英文名称: (3S,4R)-pyrrolidine-3,4-diol
• 英文别名: (3R,4S)-pyrrolidine-3,4-diol；cis-pyrrolidine-3,4-diol；cis-3,4-dihydroxy-pyrrolidine
• CAS: 131565-87-2
• 化学式: C₄H₉NO₂
• mdl: MFCD09910269
• 分子量: 103.121
• InChiKey: JCZPOYAMKJFOLA-ZXZARUISSA-N

物化性质

• 沸点：
  232.3±30.0 °C(Predicted)
• 密度：
  1.309±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  52.5
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S,4R)-吡咯烷-3,4-二醇 、 格尔德霉素 以 1,2-二氯乙烷 为溶剂， 反应 20.0h， 生成
  参考文献：
  名称：

  Synthesis and biological activities of novel 17-aminogeldanamycin derivatives

  摘要：

  Geldanamycin interferes with the action of heat shock protein 90 (Hsp90) by binding to the N-terminal ATP binding site and inhibiting an essential ATPase activity. In a program directed toward finding potent, water soluble inhibitors of Hsp90, we prepared a library of over sixty 17-alkylamino-17-demethoxygeldanamycin analogs, and compared their affinity for Hsp90, ability to inhibit growth of SKBr3 mammalian cells, and in selected cases, water solubility. Over 20 analogs showed cell growth inhibition potencies similar to that of 17-allylamino-17-demethoxygeldanamycin (17-AAG), the front-runner geldanamycin analog that is currently in multiple clinical trials. Many of these analogs showed water solubility properties that were desirable for formulation. One of the most potent and water-soluble analogs in the series was 17-(2-dimethylaminoethyl)amino-17-demethoxygeldanamycin (17-DMAG), which was independently prepared by the NCI and will soon enter clinical trials. Importantly, the binding affinity of these analogs to the molecular target Hsp90 does not correlate well with their cytotoxicity in SKBr3 cells. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.07.053
• 作为产物：
  描述：

  Benzyl cis-3,4-Dihydroxypyrrolidine-1-carboxylate 生成 (3S,4R)-吡咯烷-3,4-二醇
  参考文献：
  名称：

  [EN] QUINOLONE ANTIBACTERIAL AGENTS
  [FR] AGENTS ANTIBACTERIENS A BASE DE QUINOLONE

  摘要：

  公开了式I的化合物及其制备方法。进一步公开了制备式I生物活性化合物的方法，以及包括式I化合物的药用可接受组合物。本文公开的式I化合物可用于各种应用，包括用作抗菌剂。

  公开号：

  WO2005026165A1

文献信息

• [EN] MODULATORS OF CELLULAR ADHESION<br/>[FR] MODULATEURS DE L'ADHESION CELLULAIRE
  申请人：SUNESIS PHARMACEUTICALS INC

  公开号：WO2005044817A1

  公开（公告）日：2005-05-19

  The present invention provides compounds having formula (I): and pharmaceutically acceptable derivatives thereof, wherein R1-R4, n, p, A, B, D, E, L and AR1 are as described generally and in classes and subclasses herein, and additionally provides pharmaceutical compositions thereof, and methods for the use thereof for the treatment of disorders mediated by the CD11/CD18 family of cellular adhesion molecules (e.g., LFA-1).

  本发明提供具有以下式（I）的化合物及其药学上可接受的衍生物，其中R1-R4、n、p、A、B、D、E、L和AR1如本文中一般描述的那样，并且另外提供这些药物组合物以及用于治疗由CD11/CD18细胞粘附分子家族介导的疾病（例如LFA-1）的使用方法。
• Exocyclic Deoxyadenosine Adducts of 1,2,3,4-Diepoxybutane: Synthesis, Structural Elucidation, and Mechanistic Studies
  作者：Uthpala Seneviratne、Sergey Antsypovich、Melissa Goggin、Danae Quirk Dorr、Rebecca Guza、Adam Moser、Carrie Thompson、Darrin M. York、Natalia Tretyakova

  DOI：10.1021/tx900312e

  日期：2010.1.18

  guanine within DNA, DEB induces a large number of A → T transversions, suggesting that it forms strongly mispairing lesions at adenine nucleobases. We now report the discovery of three potentially mispairing exocyclic adenine lesions of DEB: N6,N6-(2,3-dihydroxybutan-1,4-diyl)-2′-deoxyadenosine (compound 2), 1,N6-(2-hydroxy-3-hydroxymethylpropan-1,3-diyl)-2′-deoxyadenosine (compound 3), and 1,N6-(1

  1,2,3,4-二环氧丁烷 (DEB) 被认为是 1,3-丁二烯的最终致癌代谢物，1,3-丁二烯是城市空气中存在的一种重要的工业化学品和环境污染物。虽然它优先修饰 DNA 中的鸟嘌呤，但 DEB 会诱导大量 A → T 颠换，表明它在腺嘌呤核碱基处形成强烈的错配损伤。我们现在报告了 DEB 的三个潜在错配环外腺嘌呤病变的发现：N 6 , N 6 -(2,3-dihydroxybutan-1,4-diyl)-2'-deoxyadenosine (compound 2 ), 1, N 6 -( 2-hydroxy-3-hydroxymethylpropan-1,3-diyl)-2'-deoxyadenosine (compound 3 ), and 1, N 6-(1-羟甲基-2-羟基丙烷-1,3-二基)-2'-脱氧腺苷(化合物4 )。新型 DEB-dA 加合物的结构和立体化学由紫外和核磁共振
• [EN] SUBSTITUTED N-HYDROXYAMIDINOHETEROCYCLES AS MODULATORS OF INDOLEAMINE 2,3- DIOXYGENASE<br/>[FR] N-HYDROXYAMIDINOHÉTÉROCYCLES SUBSTITUÉS EN TANT QUE MODULATEURS DE L'INDOLÉAMINE 2,3-DIOXYGÉNASE
  申请人：PHENEX DISCOVERY VERWALTUNGS GMBH

  公开号：WO2018083241A1

  公开（公告）日：2018-05-11

  The invention provides modulators of indoleamine 2,3-dioxygenase (IDO1) and their use in the prophylaxis and/or treatment of IDO1-mediated diseases. Specifically, the present invention provides compounds according to Formula (I) an enantiomer, diastereomer, tautomer or pharmaceutically acceptable salt thereof.

  本发明提供了吲哚胺2,3-双加氧酶（IDO1）的调节剂及其在预防或治疗IDO1介导的疾病中的用途。具体而言，本发明提供的是符合公式（I）的化合物、其对应的手性异构体、对映异构体、互变异构体或药用可接受的盐。
• [EN] PYRAZOLE DERIVATIVES AS SGC STIMULATORS<br/>[FR] DÉRIVÉS DE PYRAZOLE UTILISÉS COMME STIMULATEURS DE SGC
  申请人：IRONWOOD PHARMACEUTICALS INC

  公开号：WO2016044447A1

  公开（公告）日：2016-03-24

  There are described imidazole and pyrazole derivatives which are useful as stimulators of sGC, particularly NO-independent, heme-dependent stimulators. These compounds are also useful for treating, preventing or managing various disorders that are herein disclosed.

  描述了咪唑和吡唑衍生物，它们可作为sGC的刺激剂，特别是NO独立、依赖血红素的刺激剂。这些化合物还可用于治疗、预防或管理本文中披露的各种疾病。
• Synthesis and biological evaluation of pyrrolidine-functionalized nucleoside analogs
  作者：Uthpala Seneviratne、Susith Wickramaratne、Delshanee Kotandeniya、Arnold S. Groehler、Robert J. Geraghty、Christine Dreis、Suresh S. Pujari、Natalia Y. Tretyakova

  DOI：10.1007/s00044-021-02700-1

  日期：2021.2

  transcriptases and mammalian DNA polymerases by unnatural nucleoside analogs is a proven approach in antiviral and anticancer therapy, respectively. The majority of current nucleoside drugs retain the canonical nucleobase structure, which is fused to an unnatural sugar. In the present work, a series of novel pyrrolidine-functionalized purine and pyrimidine nucleosides was prepared via PyBOP-catalyzed SNAr addition-elimination

  非天然核苷类似物抑制病毒逆转录酶和哺乳动物DNA聚合酶分别是抗病毒和抗癌治疗的一种可靠方法。当前大多数核苷药物保留了与非天然糖融合的规范核碱基结构。在本工作中，通过PyBOP催化的S N制备了一系列新型的吡咯烷官能化的嘌呤和嘧啶核苷。商业卤代前体的Ar加成消除反应并测试其抗病毒和抗癌活性。新合成的核苷类似物显示出有限的生物学活性，这可能是由于它们的细胞摄取差和对相应的核苷单磷酸的生物活化效率低下的结果。HPLC-MS / MS分析显示，氨基磷酸酯前药具有改善的细胞通透性，并在人体细胞中代谢为核苷单磷酸形式。