(2R,3S)-3-苯基异丝氨酸 | 136561-53-0

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 丝氨酸类衍生物
• 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,3S)-3-苯基异丝氨酸
• 中文别名: (2R,3S)-3-苯基异丝胺酸
• 英文名称: (2R,3S)-3-phenylisoserine
• 英文别名: (2R,3S)-2-hydroxy-3-amino-3-phenylpropionic acid；(2R,3S)-3-amino-2-hydroxy-3-phenylpropanoic acid
• CAS: 136561-53-0
• 化学式: C₉H₁₁NO₃
• 分子量: 181.191
• InChiKey: RZARFIRJROUVLM-JGVFFNPUSA-N

物化性质

• 沸点：
  400.3±45.0 °C(Predicted)
• 密度：
  1.335

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  88
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 储存条件：
  2-8°C

反应信息

• 作为反应物：
  描述：

  (2R,3S)-3-苯基异丝氨酸 在 氯化亚砜 、 碳酸氢钠 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 2-hydroxy-3-(4-methyl benzenesulfonylamino)-3-phenyl-propionic acid methyl ester
  参考文献：
  名称：

  Design, synthesis of novel C-3′-N-sulfonyl modified taxane analogues from 1-deoxybaccatin VI and their impact on anti-HCC activity

  摘要：

  A new series of C-3 '-N-sulfonyl paclitaxel analogs were designed and synthesized from 1-deoxybaccatin VI and their structures were confirmed by H-1 NMR, C-13 NMR and high resolution MS. The synthesized compounds were evaluated for their in vitro anti-Hepatocellular carcinoma (HCC) activity against human hepatoma (HepG2) cell line. Bioassay results showed that compounds 17c, 17d and 17f exhibited more potent inhibitory activity against HepG2 cell line in comparison with paclitaxel. It is suggested that paclitaxel analogs containing the C-3 '-N-sulfonyl could be considered as a precursor structure for further synthesis of more potent analogues.

  DOI：

  10.1080/10286020.2019.1691999
• 作为产物：
  描述：

  2-hydroxy-3-(4-methyl benzenesulfonylamino)-3-phenyl-propionic acid methyl ester 在 氢溴酸 、 苯酚 作用下， 以 溶剂黄146 为溶剂， 反应 12.0h， 以77%的产率得到(2R,3S)-3-苯基异丝氨酸
  参考文献：
  名称：

  Catalytic Asymmetric Aminohydroxylation Provides a Short Taxol Side-chain Synthesis.

  摘要：

  The p-toluenesulfonamide derivative of the C-13 side-chain of taxol was prepared on a one third mole scale in a single step from methyl cinnamate. The process employed is catalytic asymmetric aminohydroxylation (catalytic AA). In the present case, there is no work-up other than filtration of the pure product which is insoluble in the reaction mixture. The sulfonamide protecting group is removed by acidic hydrolysis.

  DOI：

  10.3891/acta.chem.scand.50-0649

文献信息

• [EN] TARGETED THERAPEUTICS<br/>[FR] THÉRAPEUTIQUE CIBLÉE
  申请人：SYNTA PHARMACEUTICALS CORP

  公开号：WO2015038649A1

  公开（公告）日：2015-03-19

  The present invention provides pharmacological compounds including an effector moiety conjugated to a binding moiety that directs the effector moiety to a biological target of interest. Likewise, the present invention provides compositions, kits, and methods (e.g., therapeutic, diagnostic, and imaging) including the compounds. The compounds can be described as a protein interacting binding moiety-drug conjugate (SDC-TRAP) compounds, which include a protein interacting binding moiety and an effector moiety. For example, in certain embodiments directed to treating cancer, the SDC-TRAP can include an Hsp90 inhibitor conjugated to a cytotoxic agent as the effector moiety.

  本发明提供了包括与将效应子导向至感兴趣的生物靶点的结合基团共轭的药理化合物。同样，本发明提供了包括这些化合物的组合物、试剂盒和方法（例如治疗、诊断和成像）。这些化合物可以被描述为蛋白质相互作用结合基团-药物共轭（SDC-TRAP）化合物，其中包括蛋白质相互作用结合基团和效应子。例如，在针对治疗癌症的某些实施方式中，SDC-TRAP可以包括Hsp90抑制剂共轭到细胞毒性药剂作为效应子。
• SOLVATES OF DOCETAXEL
  申请人：Cieslinski Witold Stanislaw

  公开号：US20120071674A1

  公开（公告）日：2012-03-22

  The present invention provides solvates of 4-acetoxy-2α-benzoyloxy-5β,20-epoxy-1,7β,10β-trihydroxy-9-oxo-tax-11-en-13α-yl (2R,3S)-3-tert-butoxycarbonylamino-2-hydroxy-3-phenylpropionate and C2-3-alkyl esters of formic acid, process of their preparation and their use in the synthesis of the pharmaceutically pure 4-acetoxy-2α-benzoyloxy-5β,20-epoxy-1,7β,10β-trihydroxy-9-oxo-tax-11-en-13α-yl (2R,3S)-3-tert-butoxycarbonylamino-2-hydroxy-3-phenylpropionate.

  本发明提供了4-乙酰氧基-2α-苯甲酰氧基-5β,20-环氧-1,7β,10β-三羟基-9-酮基-紫杉醇-11-烯-13α-基(2R,3S)-3-叔丁氧羰基氨基-2-羟基-3-苯基丙酸的溶剂结晶体及甲酸C2-3-烷基酯，其制备方法以及它们在合成药用纯度的4-乙酰氧基-2α-苯甲酰氧基-5β,20-环氧-1,7β,10β-三羟基-9-酮基-紫杉醇-11-烯-13α-基(2R,3S)-3-叔丁氧羰基氨基-2-羟基-3-苯基丙酸中的应用。
• Preparation and Use of Aziridino Alcohols as Promoters for the Enantioselective Addition of Dialkylzinc Reagents to <i>N</i>-(Diphenylphosphinoyl) Imines
  作者：Pher G. Andersson、David Guijarro、David Tanner

  DOI：10.1021/jo970918h

  日期：1997.10.1

  chiral aziridino alcohols 2-5 has been synthesized starting from either readily available amino acids (L-serine, L-threonine, and allo-L-threonine) or simple olefins (using Sharpless asymmetric aminohydroxylation and dihydroxylation reactions). Chiral ligands 2-5 have been tested as promoters for the enantioselective addition of dialkylzinc reagents to N-(diphenylphosphinoyl) imines 1. The influence

  已从容易获得的氨基酸（L-丝氨酸，L-苏氨酸和别-L-苏氨酸）或简单烯烃（使用Sharpless不对称氨基羟基化和二羟基化反应）开始合成了一组手性叠氮基醇2-5。已测试手性配体2-5作为促进剂，用于将二烷基锌试剂对映选择性加成到N-（二苯基膦酰基）亚胺1上。研究了取代基对氮丙啶环和醇部分的选择性的影响，并且在最佳条件下在这种情况下，可获得高达94％的对映体过量。最初形成的N-保护的胺6的酸性水解导致相应的游离胺7没有外消旋化。尽管使用了化学计量的配体，大约90％的蛋白质可以在后处理过程中回收并重复使用，而不会造成手性诱导的明显损失。还已经评估了叠氮基叠氮醇2-5作为用于相同反应的催化剂的效用，并且使用0.25当量的手性配体实现了高达76％的对映体过量。还提出了加成反应的可能过渡态。
• Lipase-catalyzed Transesterification of Methyl 2-Substituted 3-Hydroxy-4-pentenoates and its Synthetic Application to the Taxol Side Chain
  作者：Tadakatsu Mandai、Tetsuta Oshitari、Masafumi Susowake

  DOI：10.1055/s-2002-34247

  日期：——

  Syn-and anti-methyl 2-substituted 3-hydroxy-4-pentenoates were efficiently resolved in lipase-catalyzed transesterification. This protocol was successfully applied to the synthesis of the taxol side chain.

  辛基和反式甲基2取代的3-羟基-4-戊烯酸酯在脂酶催化的转酯化反应中高效分离。该方法成功应用于紫杉醇侧链的合成。
• Synthesis and biological activity of C-7, C-9 and C-10 modified taxane analogues from 1-deoxybaccatin VI
  作者：Chenghu Xie、Yongmei Cui、Lanlan Li、Minmin Zhang、Hongchun Liu、Haixia Lin

  DOI：10.1016/j.bmc.2020.115736

  日期：2020.11

  A series of C-7, C-9 and C-10 modified taxane analogues were synthesized and their in vitro anticancer activities against three human cancer cell lines: A-549 (human lung cancer cell line), MDA-MB-231 (human breast cancer cell line), A-549/T (human lung cancer resistant cell line) were studied. The novel 1-deoxybaccatin VI derivatives modified with carbonate group at C-9 and C-10 positions enable the

  合成了一系列经C-7，C-9和C-10修饰的紫杉烷类似物，它们对三种人类癌细胞系：A-549（人类肺癌细胞系），MDA-MB-231（人类）具有体外抗癌活性。乳腺癌细胞系），A-549 / T（抗人肺癌细胞系）进行了研究。在C-9和C-10位置用碳酸酯基修饰的新型1-脱氧浆果赤霉素VI衍生物使这些化合物的行为与其他类似化合物明显不同。新合成的紫杉烷类似物在这三种细胞系中，特别是在耐药细胞系中具有很强的细胞毒性，表明它们是抗癌药物设计的潜在先导化合物。