N-(对甲苯磺酰基)苏氨酸 | 34235-88-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-(对甲苯磺酰基)苏氨酸
• 英文名称: (L)-N-Tosylthreonine
• 英文别名: N-(p-tolylsulfonyl)threonine；(2S,3S)-3-hydroxy-2-(4-methylphenylsulfonamido)butanoic acid；TsthrH2；N^α-Tos-Thr；N-(toluene-4-sulfonyl)-L_S-threonine；N-(Toluol-4-sulfonyl)-L_S-threonin；N-tosyl-L-threonine；(2S,3R)-3-hydroxy-2-[(4-methylphenyl)sulfonylamino]butanoic acid
• CAS: 34235-88-6
• 化学式: C₁₁H₁₅NO₅S
• 分子量: 273.31
• InChiKey: SZILOGOOPIXJAQ-SCZZXKLOSA-N

物化性质

• 熔点：
  130 °C
• 沸点：
  489.4±55.0 °C(Predicted)
• 密度：
  1.375±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  112
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(对甲苯磺酰基)苏氨酸 在 盐酸 作用下， 生成 L-苏氨酸
  参考文献：
  名称：

  酶促肽合成。3. Mitteilung。肽胆碱DL-苏氨酸-异丙酯

  摘要：

  胰蛋白酶的苏糖异丁酸酯。

  DOI：

  10.1002/hlca.19510340652
• 作为产物：
  描述：

  对甲苯磺酰氯 在 马钱子碱 作用下， 生成 N-(对甲苯磺酰基)苏氨酸
  参考文献：
  名称：

  酶促肽合成。3. Mitteilung。肽胆碱DL-苏氨酸-异丙酯

  摘要：

  胰蛋白酶的苏糖异丁酸酯。

  DOI：

  10.1002/hlca.19510340652
• 作为试剂：
  描述：

  苯乙烯 在 1,3-二氯-5,5-二甲基海因 、 N-(对甲苯磺酰基)苏氨酸 、 水 作用下， 以 丙酮 为溶剂， 反应 1.0h， 以93%的产率得到(±)-2-氯-1-苯基乙醇
  参考文献：
  名称：

  烯烃的高度区域和非对映选择性卤代羟基化：邻位卤代醇的简便合成

  摘要：

  基于各种具有给电子或吸电子取代基的烯烃的直接卤代羟基化，已经开发了一种用于合成邻位氯醇或溴代醇衍生物的有效方法。该反应在温和条件下在的存在下进行Ñ甲苯磺酰升-苏氨酸（NTsLT）作为酸性添加剂使用氯胺-T三水合物，1,3-二氯-5,5-二甲基（DCDMH）或ñ -bromoacetamide（ AcNHBr）作为卤素源，分别以高至高收率提供相应的邻位卤代醇，并具有出色的区域选择性和立体选择性。

  DOI：

  10.1016/j.tet.2011.06.077

文献信息

• Synthesis of Optically Active 3-Amino-2,3-dihydrobenzopyran-4-ones by Ring Transformation of Aziridinecarboxamides
  作者：Karsten Woydowski、Jürgen Liebscher

  DOI：10.1055/s-2000-7101

  日期：——

  Weinreb amides 1 of aziridinecarboxylic acids react with o-lithiated O-methoxymethylphenols 2 to 2-benzoylaziridines 3 which, after O-deprotection, undergo ring transformation by attack of the phenolic hydroxy group at 3-position of the aziridine ring affording optically active 3-aminodihydrobenzopyran-4-ones 5 under acidic conditions. Alternatively, 5-membered benzofuran-3-ones 6 and 7 can be obtained under basic conditions.

  氮丙啶羧酸的 Weinreb 酰胺 1 与邻锂化的 O-甲氧基甲基苯酚 2 反应生成 2-苯甲酰氮丙啶 3，后者在 O-脱保护后，通过攻击氮丙啶环 3 位的酚羟基进行环转化，得到光学活性 3-氨基二氢苯并吡喃-4-酮5在酸性条件下。或者，可以在碱性条件下获得5元苯并呋喃-3-酮6和7。
• Second cycle asymmetric dihydroxylation reaction
  申请人：The Scripps Research Institute

  公开号：US20020042545A1

  公开（公告）日：2002-04-11

  A process for catalyzing asymmetric dihydroxylations of olefins employs an Os(VI) complex as a catalytic intermediate in the formation of chiral vicinal diol products. The process requires a chiral bidentate ligand that favors diol formation in the “second cycle” of asymmetric dihydroxylation.

  一种催化烯烃不对称二羟基化的工艺采用 Os(VI) 复合物作为催化中间体，形成手性邻位二元醇产物。该工艺需要一种手性双齿配体，这种配体有利于在不对称二羟基化的 "第二循环 "中形成二元醇。
• Synthesis and Structure–Activity Relationships of Arylsulfonamides as AIMP2-DX2 Inhibitors for the Development of a Novel Anticancer Therapy
  作者：Aneesh Sivaraman、Dae Gyu Kim、Deepak Bhattarai、Minkyoung Kim、Hwa Young Lee、Semi Lim、Jiwon Kong、Ja-il Goo、Seunghwan Shim、Seungbeom Lee、Young-Ger Suh、Yongseok Choi、Sunghoon Kim、Kyeong Lee

  DOI：10.1021/acs.jmedchem.9b01961

  日期：2020.5.28

  AIMP2-DX2, a splicing variant of AIMP2, is up-regulated in lung cancer, possesses oncogenic activity, and results in tumorigenesis. Specifically inhibiting the interaction between AIMP2-DX2 and HSP70 to suppress AIMP2-DX2-dependent cancers with small molecules is considered a promising avenue for cancer therapeutics. Optimization of hit BC-DXI-04 (IC50 = 40.1 mu M) provided new potent sulfonamide based AIMP2-DX2 inhibitors. Among these, BC-DXI-843 showed improved inhibition against AIMP2-DX2 (IC50 = 0.92 mu M) with more than 100-fold selectivity over AIMP2 in a luciferase assay. Several binding assays indicated that this compound effectively induces cancer cell apoptosis by specifically interrupting the interaction between DX2 and HSP70, which leads to the degradation of DX2 via Siah1-mediated ubiquitination. More importantly, BC-DXI-843 demonstrated in vivo efficacy in a tumor xenograft mouse model (H460 cells) at a dosage of 50 mg/kg, suggesting it as a promising lead for development of novel therapeutics targeting AIMP2-DX2 in lung cancer.
• Syntheses of actinomycin and analogs. VIII. Synthesis of actinomycin D lactam
  作者：Eric Atherton、Johannes Meienhofer

  DOI：10.1021/ja00768a070

  日期：1972.6
• Synthesis, characterization, and cytotoxicity of complexes of palladium(II) with 1,4-diaminobutane/1,3-diaminopropane and 4-toluenesulfonyl-<scp>L</scp>-amino acid dianion
  作者：Lili Ma、Jinchao Zhang、Fangfang Zhang、Chao Chen、Luwei Li、Shuxiang Wang、Shenghui Li

  DOI：10.1080/00958972.2012.713102

  日期：2012.9.20

  Eight new palladium(II) complexes with 4-toluenesulfonyl-L-amino acid dianion and 1,4-dab/1,3-dap, [Pd(1,4-dab)(TsglyNO)] center dot H2O (1), [Pd(1,4-dab)(TsvalNO)] (2), [Pd(1,4-dab)(TsleuNO)] (3), [Pd(1,4-dab)(TsileNO)] (4), [Pd(1,4-dab)(TsserNO)] center dot 0.5H(2)O (5), [Pd(1,4-dab)(TspheNO)] center dot 0.5H(2)O (6), [Pd(1,4-dab)(TsthrNO)] center dot H2O (7), and [Pd(1,3-dap)(TsserNO)] (8), have been synthesized and characterized by elemental analysis, IR, UV, H-1 NMR, and mass spectrometry. Crystal structure of 8 has been determined by X-ray diffraction. The cytotoxicities were tested by MTT assay. The results indicate the complexes exert cytotoxic effects against HL-60 and Bel-7402. The structure-activity relationship suggests that both amino acids and N-containing ligands have important effects on cytotoxicity, but the IC50 values do not show definite correlation with variation of these ligands.