tert-butyl 3,4-dihydroxypiperidine-1-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: tert-butyl 3,4-dihydroxypiperidine-1-carboxylate
• 英文别名: cis-tert-butyl 3,4-dihydroxypiperidine-1-carboxylate；(±)-N-boc-cis-3,4-piperidinediol；tert-butyl (3RS,4SR)-3,4-dihydroxy-1-piperidinecarboxylate；Tert-butyl cis-3,4-dihydroxypiperidine-1-carboxylate；tert-butyl (3S,4R)-3,4-dihydroxypiperidine-1-carboxylate
• 化学式: C₁₀H₁₉NO₄
• 分子量: 217.265
• InChiKey: RIZGRNBWPJMDKU-SFYZADRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  70
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl 3,4-dihydroxypiperidine-1-carboxylate 在 盐酸 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 3-(4-aminophenyl)-1-(cis-3,4-dihydroxypiperidin-1-yl)propan-1-one hydrochloride
  参考文献：
  名称：

  Synthesis, molecular modeling and evaluation of α-glucosidase inhibition activity of 3,4-dihydroxy piperidines

  摘要：

  Biological evaluation of 3,4-dihydroxy piperidines as alpha-glucosidase inhibitors is being reported for the first time. Forty-five derivatives (amides, di-amides and sulfonamides) were made using cis and trans 3,4-dihydroxy piperidines to evaluate their alpha-glucosidase inhibition activity. Polar groups (-OH, -NH2) on phenyl ring having derivatives 5i, 5l, 7g, 7i & 12j showed excellent activity compared to standard references. Acarbose, Voglibose and Miglitol were used as standard references. Molecular docking simulations were done for compounds to identify important binding modes responsible for inhibition activity of alpha-glucosidase. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.02.072
• 作为产物：
  描述：

  1,2,3,6-四氢吡啶 在 potassium osmate(VI) dihydrate 、 sodium carbonate 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 为溶剂， 反应 22.0h， 生成 tert-butyl 3,4-dihydroxypiperidine-1-carboxylate
  参考文献：
  名称：

  Synthesis, molecular modeling and evaluation of α-glucosidase inhibition activity of 3,4-dihydroxy piperidines

  摘要：

  Biological evaluation of 3,4-dihydroxy piperidines as alpha-glucosidase inhibitors is being reported for the first time. Forty-five derivatives (amides, di-amides and sulfonamides) were made using cis and trans 3,4-dihydroxy piperidines to evaluate their alpha-glucosidase inhibition activity. Polar groups (-OH, -NH2) on phenyl ring having derivatives 5i, 5l, 7g, 7i & 12j showed excellent activity compared to standard references. Acarbose, Voglibose and Miglitol were used as standard references. Molecular docking simulations were done for compounds to identify important binding modes responsible for inhibition activity of alpha-glucosidase. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.02.072

文献信息

• SYNTHESIS AND APPLICATION OF CHIRAL SUBSTITUTED POLYVINYLPYRROLIDINONES
  申请人：Kansas State University Research Foundation

  公开号：US20200306737A1

  公开（公告）日：2020-10-01

  Chiral polyvinylpyrrolidinone (CSPVP), complexes of CSPVP with a core species, such as a metallic nanocluster catalyst, and enantioselective oxidation reactions utilizing such complexes are disclosed. The CSPVP complexes can be used in asymmetric oxidation of diols, enantioselective oxidation of alkenes, and carbon-carbon bond forming reactions, for example. The CSPVP can also be complexed with biomolecules such as proteins, DNA, and RNA, and used as nanocarriers for siRNA or dsRNA delivery.

  手性聚乙烯吡咯烷酮（CSPVP），CSPVP与金属纳米团簇催化剂等核心物种形成的络合物，以及利用这种络合物进行对映选择氧化反应的方法被揭示。CSPVP络合物可用于不对称二醇氧化、烯烃对映选择氧化以及碳-碳键形成反应等。CSPVP还可以与蛋白质、DNA和RNA等生物分子形成络合物，并用作siRNA或dsRNA传递的纳米载体。
• [EN] PYRAZOLO[1,5-A]PYRIMIDINE-5,7-DIAMINE COMPOUNDS AS CDK INHIBITORS AND THEIR THERAPEUTIC USE<br/>[FR] PYRAZOLO[1,5-A]PYRIMIDINE-5,7-DIAMINES EN TANT QU'INHIBITEURS DE CDK ET LEUR UTILISATION THÉRAPEUTIQUE
  申请人：CANCER REC TECH LTD

  公开号：WO2015124941A1

  公开（公告）日：2015-08-27

  The present invention pertains generally to the field of therapeutic compounds. More specifically the present invention pertains to certain pyrazolo[1,5-a]pyrimidine-5,7- diamine compounds (referred to herein as "PPDA compounds") that, inter alia, inhibit (e.g., selectively inhibit) CDK (e.g., CDK1, CDK2, CDK4, CDK5, CDK6, CDK7, CDK8, CDK9, CDK10, CDK11, CDK12, CDK13, etc.). The present invention also pertains to pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions, both in vitro and in vivo, to inhibit CDK; and to treat disorders including: disorders that are associated with CDK; disorders that result from an inappropriate activity of a cyclin-dependent kinase (CDK); disorders that are associated with CDK mutation; disorders that are associated with CDK overexpression; disorders that are associated with upstream pathway activation of CDK; disorders that are ameliorated by the inhibition of CDK; proliferative disorders; cancer; viral infections (including HIV); neurodegenerative disorders (including Alzheimer's disease and Parkinson's disease); ischaemia; renal diseases; and cardiovascular disorders (including atherosclerosis). Optionally, the treatment further comprises treatment (e.g., simultaneous or sequential treatment) with a further active agent which is, e.g., an aromatase inhibitor, an anti-estrogen, a Her2 blocker, a cytotoxic chemotherapeutic agent, etc.

  本发明一般涉及治疗化合物领域。更具体地，本发明涉及某些吡唑并[1,5-a]嘧啶-5,7-二胺化合物（以下简称为“PPDA化合物”），其在一定程度上抑制（例如，选择性抑制）CDK（例如CDK1、CDK2、CDK4、CDK5、CDK6、CDK7、CDK8、CDK9、CDK10、CDK11、CDK12、CDK13等）。本发明还涉及包含这些化合物的药物组合物，以及使用这些化合物和组合物，无论是体外还是体内，来抑制CDK；并用于治疗包括：与CDK相关的疾病；由于细胞周期依赖性激酶（CDK）不适当活性而导致的疾病；与CDK突变相关的疾病；与CDK过表达相关的疾病；与上游通路激活CDK相关的疾病；通过抑制CDK改善的疾病；增生性疾病；癌症；病毒感染（包括HIV）；神经退行性疾病（包括阿尔茨海默病和帕金森病）；缺血；肾脏疾病；和心血管疾病（包括动脉粥样硬化）等疾病。可选地，治疗还进一步包括与另一活性药剂（例如芳香化酶抑制剂、抗雌激素、Her2阻断剂、细胞毒性化疗药物等）一起进行治疗（例如同时或顺序治疗）。
• Selective Isomerization via Transient Thermodynamic Control: Dynamic Epimerization of <i>trans</i> to <i>cis</i> Diols
  作者：Christian J. Oswood、David W. C. MacMillan

  DOI：10.1021/jacs.1c11552

  日期：2022.1.12

  Traditional approaches to stereoselective synthesis require high levels of enantio- and diastereocontrol in every step that forms a new stereocenter. Here, we report an alternative approach, in which the stereochemistry of organic substrates is selectively edited without further structural modification, a strategy with the potential to allow new classes of late-stage stereochemical manipulation and

  传统的立体选择性合成方法需要在形成新立体中心的每一步中进行高水平的对映体和非对映体控制。在这里，我们报告了一种替代方法，其中有机底物的立体化学被选择性地编辑而无需进一步的结构修饰，这种策略有可能允许新类别的后期立体化学操作并提供稀有或有价值的立体化学构型。在这项工作中，我们描述了通过氢原子转移光催化和硼酸介导的瞬态热力学控制实现环状二醇的选择性差向异构化，选择性地从原本受欢迎的反式异构体生成不太稳定的顺式产物。一系列取代模式和环尺寸适合选择性异构化，包括立体化学复杂的多元醇，例如雌三醇，以及无环邻位二醇的顺式差向异构化。此外，该策略使得糖端基异构体能够发生不同的差向异构化，从而可以从α-或β-构型糖苷获得不同的糖异构体。
• Synthesis of functionalized nitrogen heterocycles from β- and γ-amino acids by radical decarboxylation
  作者：Alicia Boto、Rosendo Hernández、Yolanda de León、José R. Murguı́a、Abigail Rodrı́guez-Afonso

  DOI：10.1016/j.tetlet.2004.07.111

  日期：2004.9

  The radical decarboxylation of β- and γ-amino acids on treatment with PhI(OAc)2–I2 is a mild and efficient methodology to synthesize halogenated or oxygenated nitrogen heterocycles. The reaction was applied to the synthesis of bioactive products, such as opioid analogues, iminosugars and new antifungic agents.

  用PhI（OAc）2 –I 2处理β-和γ-氨基酸的自由基脱羧是合成卤化或氧合氮杂环的温和有效方法。该反应被用于生物活性产物的合成，例如阿片类似物，亚氨基糖和新的抗真菌剂。
• Diamine Derivatives
  申请人：Ohta Toshiharu

  公开号：US20110312990A1

  公开（公告）日：2011-12-22

  A compound represented by the general formula (1): -Q 1 -Q 2 -T 0 -N(R 1 )-Q 3 -N(R 2 )-T 1 -Q 4 (1) wherein R 1 and R 2 are hydrogen atoms or the like; Q 1 is a saturated or unsaturated, 5- or 6-membered cyclic hydrocarbon group which may be substituted, or the like; Q 2 is a single bond or the like; Q 3 is a group in which Q 5 is an alkylene group having 1 to 8 carbon atoms, or the like; and T 0 and T 1 are carbonyl groups or the like; a salt thereof, a solvate thereof, or an N-oxide thereof. The compound is useful as an agent for preventing and/or treating cerebral infarction, cerebral embolism, myocardial infarction, angina pectoris, pulmonary infarction, pulmonary embolism, Buerger's disease, deep venous thrombosis, disseminated intravascular coagulation syndrome, thrombus formation after valve or joint replacement, thrombus formation and reocclusion after angioplasty, systemic inflammatory response syndrome (SIRS), multiple organ dysfunction syndrome (MODS), thrombus formation during extracorporeal circulation, or blood clotting upon blood drawing.

  化合物的一般式表示为(1)：-Q1-Q2-T0-N(R1)-Q3-N(R2)-T1-Q4(1)，其中R1和R2为氢原子或类似物；Q1为饱和或不饱和的5-或6-成员环烃基，可以是取代基或类似物；Q2为单键或类似物；Q3为其中Q5为1至8个碳原子的烷基或类似物的基团；T0和T1为羰基或类似物。该化合物及其盐、溶剂化物或N-氧化物可用于预防和/或治疗脑梗死、脑栓塞、心肌梗死、心绞痛、肺梗死、肺栓塞、布尔格病、深静脉血栓形成、弥散性血管内凝血综合征、瓣膜或关节置换后的血栓形成、血管成形术后的血栓形成和再闭塞、全身性炎症反应综合征(SIRS)、多器官功能障碍综合征(MODS)、体外循环期间的血栓形成或采血时的血液凝固。