(2R,4R)-1-叔丁氧羰基-4-羟基哌啶-2-羧酸 | 441044-11-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: (2R,4R)-1-叔丁氧羰基-4-羟基哌啶-2-羧酸
• 英文名称: (4R)-1-(tert-butoxycarbonyl)-4-hydroxypiperidine-2-carboxylic acid
• 英文别名: (2R,4R)-1-tert-Butoxycarbonyl-4-hydroxypiperidine-2-carboxylic acid；(2R,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]piperidine-2-carboxylic acid
• CAS: 441044-11-7
• 化学式: C₁₁H₁₉NO₅
• 分子量: 245.276
• InChiKey: GCAZZUFIDGXTDA-HTQZYQBOSA-N

物化性质

• 密度：
  1.264

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  87.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,4R)-1-叔丁氧羰基-4-羟基哌啶-2-羧酸 在 palladium 10% on activated carbon 、 氢气 、 三乙胺 、 三氟乙酸 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 45.0h， 生成 ethyl (2S,4R)-4-[({2-[(1R,3R)-1-acetoxy-3-{[(2S)-2-({[(2R,4R)-4-hydroxy-1-methylpiperidin-2-yl]-carbonyl}amino)-3-methylbutanoyl](methyl)amino}-4-methylpentyl]-1,3-thiazol-4-yl}carbonyl)amino]-2-methyl-5-phenylpentanoate
  参考文献：
  名称：

  改进的微管溶素的全合成以及对癌细胞具有高效细胞毒性的新型微管溶素的设计、合成和生物学评价，作为抗体-药物偶联物的潜在有效载荷

  摘要：

  V (Tb45) 和 U (Tb46) 和 pretubulysin D (PTb-D43) 等天然微管溶素的改进、简化的全合成，以及它们在合成设计的微管溶素类似物（Tb44、PTb-D42、PTb-D47-PTb）中的应用-D49 和 Tb50-Tb120)，进行了描述。合成化合物对某些癌细胞系的细胞毒性评估揭示了许多具有特殊效力的新型类似物[例如，Tb111：IC50 = 40 pM 对 MES SA（子宫肉瘤）细胞系；针对 HEK 293T（人胚胎肾癌）细胞系的 IC50 = 6 pM；和 IC50 = 1.54 nM，对 MES SA DX（具有明显多重耐药性的 MES SA）细胞系]。这些研究产生了一组有价值的构效关系，为进一步的分子设计、合成和生物学评价研究提供指导。

  DOI：

  10.1021/jacs.7b12692
• 作为产物：
  描述：

  1-phenylethylammonium (2R,4R)-1-(tert-butoxycarbonyl)-4-hydroxypiperidine-2-carboxylate 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 生成 (2R,4R)-1-叔丁氧羰基-4-羟基哌啶-2-羧酸
  参考文献：
  名称：

  [EN] INHIBITORS OF SPHINGOSINE KINASE 1
  [FR] INHIBITEURS DE LA SPHINGOSINE KINASE 1

  摘要：

  公开号：

  WO2010033701A3

文献信息

• QUINAZOLINE DERIVATIVES AS TYROSINE KINASE INHIBITORS
  申请人：Halsall Christopher Thomas

  公开号：US20110152297A1

  公开（公告）日：2011-06-23

  The invention concerns quinazoline derivatives of the Formula I, or pharmaceutically acceptable salts thereof: wherein each of R 1 , R 2 , R 3 , R 4 and m are as defined in the description; processes for their preparation; pharmaceutical compositions containing them and their use in the manufacture of a medicament for providing an anti-proliferative effect. The quinazoline derivatives of Formula I are expected to be useful in the treatment of diseases such as certain cancers mediated by erbB receptor tyrosine kinases, and, for example, EGFR tyrosine kinase.

  本发明涉及公式I的喹唑啉衍生物或其药学上可接受的盐：其中R1，R2，R3，R4和m的定义如描述中所定义；其制备方法；含有它们的制药组合物以及它们用于制造抗增殖效应药物的用途。公式I的喹唑啉衍生物预计可用于治疗某些由erbB受体酪氨酸激酶介导的癌症，例如EGFR酪氨酸激酶。
• INHIBITORS OF SPHINGOSINE KINASE 1
  申请人：Xiang Yibin

  公开号：US20110275673A1

  公开（公告）日：2011-11-10

  The invention relates to compounds of Formula (I). Compounds of the present invention are inhibitors of sphingosine kinase 3, and are useful in the treatment of various disorders and conditions, such as inflammatory disorders.

  本发明涉及公式（I）的化合物。本发明的化合物是鞘氨醇激酶3的抑制剂，并且在治疗各种疾病和病况，例如炎症性疾病方面非常有用。
• [EN] TUBULYSIN ANALOGUES AS ANTICANCER AGENTS AND PAYLOADS FOR ANTIBODY-DRUG CONJUGATES AND METHODS OF TREATMENT THEREWITH<br/>[FR] ANALOGUES DE TUBULYSINE EN TANT QU'AGENTS ANTICANCÉREUX ET CHARGES UTILES POUR DES CONJUGUÉS ANTICORPS-MÉDICAMENT ET PROCÉDÉS DE TRAITEMENT ASSOCIÉS
  申请人：UNIV RICE WILLIAM M

  公开号：WO2019108685A8

  公开（公告）日：2019-09-06
• Chemoenzymatic Synthesis of the Four Diastereoisomers of 4-Hydroxypipecolic Acid from <i>N</i>-Acetyl-(<i>R</i>,<i>S</i>)-allylglycine:  Chiral Scaffolds for Drug Discovery
  作者：Richard C. Lloyd、Mark E. B. Smith、Dean Brick、Stephen J. C. Taylor、David A. Chaplin、Raymond McCague

  DOI：10.1021/op020017x

  日期：2002.11.1

  All four diastereoisomers of 4-hydroxypipecolic acid were prepared in a form conveniently protected for drug discovery applications with the use of industrially scaleable methodology. Resolution of the racemic starting material using proprietary acylases followed by an acyliminium ion cyclisation gave diastereomeric mixtures of 4-formyloxypipecolic acid, which were differentiated using an enzyme-catalysed hydrolysis. The products were separated, by partition, and by following a sequence of straightforward chemical steps, the individual stereoisomers of the protected 4-hydroxypipecolates were crystallized to optical purity in 100 g quantities.
• TUBULYSIN ANALOGUES AS ANTICANCER AGENTS AND PAYLOADS FOR ANTIBODY-DRUG CONJUGATES AND METHODS OF TREATMENT THEREWITH
  申请人：William Marsh Rice University

  公开号：US20210188906A1

  公开（公告）日：2021-06-24

  In one aspect, the present disclosure provides tubulysin analogs of the formula (I) wherein the variables are as defined herein. In another aspect, the present disclosure also provides methods of preparing the compounds disclosed herein. In another aspect, the present disclosure also provides pharmaceutical compositions and methods of use of the compounds disclosed herein. Additionally, drug conjugates with cell targeting moieties of the compounds are also provided.