N-methyl-L-threonine methyl ester | 95599-23-8

• 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
• 英文名称: N-methyl-L-threonine methyl ester
• 英文别名: (2S,3R)-methyl 3-hydroxy-2-(methylamino)butanoate；methyl (2S,3R)-3-hydroxy-2-(methylamino)butanoate
• CAS: 95599-23-8
• 化学式: C₆H₁₃NO₃
• 分子量: 147.174
• InChiKey: BZTAVCVTBAXONH-UHNVWZDZSA-N

物化性质

• 沸点：
  231.3±25.0 °C(Predicted)
• 密度：
  1.065±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-methyl-L-threonine methyl ester 在 盐酸 作用下， 反应 16.0h， 生成 N-甲基L-苏氨酸
  参考文献：
  名称：

  Papuamides A−D, HIV-Inhibitory and Cytotoxic Depsipeptides from the Sponges Theonella mirabilis and Theonella swinhoei Collected in Papua New Guinea

  摘要：

  The novel cyclic depsipeptides papuamides A (1), B (2), C (3), and D (4) have been isolated from Papua New Guinea collections of the sponges Theonella mirabilis and Theonella swinhoei. Their structures were determined by a combination of spectroscopic analysis and chemical degradation and derivatization studies. In addition to glycine, alanine, and threonine, these peptides contain a number of unusual amino acids including 3,4-dimethylglutamine, beta-methoxytyrosine, 3-methoxyalanine, and 2,3-diaminobutanoic acid or 2-amino-2-butenoic acid residues. Papuamides A-D (1-4) are also the first marine-derived peptides reported to contain 3-hydroxyleucine and homoproline residues. These peptides also contain a previously undescribed 2,3-dihydroxy-2,6,8-trimethyldeca-(4Z,6E)-dienoic acid moiety N-linked to a terminal glycine residue. Papuamides A (1) and B (2) inhibited the infection of human T-lymphoblastoid cells by HIV-1(RF) in vitro with an EC50 of approximately 4 ng/mL. Compound 1 was also cytotoxic against a panel of human cancer cell lines with a mean IC50 of 75 ng/mL.

  DOI：

  10.1021/ja990582o
• 作为产物：
  描述：

  甲基(4S,5R)-5-甲基-1,3-恶唑烷-4-羧酸酯 在 三乙基硅烷 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 N-methyl-L-threonine methyl ester
  参考文献：
  名称：

  Beulshausen, Tessa; Groth, Ulrich; Schoellkopf, Ulrich, Liebigs Annalen der Chemie, 1992, # 5, p. 523 - 526

  摘要：

  DOI：

文献信息

• Stereoelectronic control of oxazolidine ring-opening: structural and chemical evidences
  作者：Jimmy Sélambarom、Sophie Monge、Francis Carré、Jean Pierre Roque、André A Pavia

  DOI：10.1016/s0040-4020(02)01287-5

  日期：2002.11

  Ring opening of oxazolidines derived from tris(hydroxymethyl)aminomethane, l-serine and l-threonine was investigated. It was shown that n(N)→σ∗(C–O) electron delocalization (endo-anomeric effect) occurring in the five-membered ring plays a major role in the cleavage of the intracyclic C–O bond. The present work establishes that when the nitrogen lone pair is conjugated with a carbonyl group (n(N)→π(CO)

  研究了由三（羟甲基）氨基甲烷，L-丝氨酸和L-苏氨酸衍生的恶唑烷的开环。结果表明，在五元环中发生的n（N）→σ ∗（C–O）电子离域作用（内消旋作用）在环内C-O键的裂解中起主要作用。目前的工作表明，当氮孤对与羰基结合时（n（N）→π（CO）离域），就像在N-酰基恶唑烷中发生的那样，水解和还原性开环都变得非常困难。氧碱性降低和环内C-O键强度升高的结果。
• Facile Synthesis of Highly Functionalized <i>N-</i>Methyl Amino Acid Esters without Side-Chain Protection
  作者：Kimberly N. White、Joseph P. Konopelski

  DOI：10.1021/ol051441w

  日期：2005.9.1

  [reaction: see text] The facile, two-pot synthesis of N-methyl amino acid esters by way of reductive amination is presented. Side chain protection schemes are not required, the starting materials are all commercially available, and the synthetic method is straightforward and affords desired product in very high yield.

  [反应：见正文]提出了一种通过还原胺化的简便，两锅法合成N-甲基氨基酸酯的方法。不需要侧链保护方案，起始原料都是可商购的，并且合成方法是直接的并且可以非常高的产率提供所需的产物。
• Total synthesis and biological studies of cryptocin and derivatives of equisetin and fusarisetin A
  作者：Lili Kong、Mingjin Rao、Jinjie Ou、Jun Yin、Weiqiang Lu、Mingyao Liu、Xiufeng Pang、Shuanhu Gao

  DOI：10.1039/c4ob01149j

  日期：——

  Total synthesis of cryptocin, derivatives of equisetin and fusarisetin A were achieved based on the biosynthetic hypothesis. The biological studies of their inhibitory effects on breast cancer cells (MDA-MB-231) survival and metastasis were further investigated.

  基于生物合成假设，成功合成了cryptocin、equisetin衍生物和fusarisetin A。进一步研究了它们对乳腺癌细胞（MDA-MB-231）存活和转移的抑制效果。
• [EN] IMMUNOMODULATOR COMPOUNDS<br/>[FR] COMPOSÉS IMMUNOMODULATEURS
  申请人：CHEMOCENTRYX INC

  公开号：WO2019023575A1

  公开（公告）日：2019-01-31

  Compounds are provided that are useful as immunomodulators. The compounds have the following Formula (I) including stereoisomers and pharmaceutically acceptable salts thereof, wherein Z, L, R1a, R1b, R1c, R1d, R2a, R2b, R2c, R3, R4, R5, R6a, R6b, m and n are as defined herein. Methods associated with preparation and use of such compounds, as well as pharmaceutical compositions comprising such compounds, are also disclosed.

  提供了作为免疫调节剂有用的化合物。这些化合物具有以下的化学式（I），包括其立体异构体和药用盐，其中Z、L、R1a、R1b、R1c、R1d、R2a、R2b、R2c、R3、R4、R5、R6a、R6b、m和n的定义如本文所述。还公开了与这些化合物的制备和使用相关的方法，以及包含这些化合物的药物组合物。
• [EN] METHODS OF TREATING CANCER WITH SMALL MOLECULE PD-L1 INHIBITORS<br/>[FR] MÉTHODES DE TRAITEMENT DU CANCER AVEC DES INHIBITEURS DE PD-L1 À PETITES MOLÉCULES
  申请人：CHEMOCENTRYX INC

  公开号：WO2020047035A1

  公开（公告）日：2020-03-05

  The present disclosure provides, inter alia, methods of treating cancer by administering an effective amount of a compound of Formula (I). In some embodiments, the cancer is a solid cancer. In some embodiments, the cancer is melanoma. In some aspects, the present disclosure provides methods of increasing the CD8+ T cell/CD4+ T cell ratio in a solid tumor microenvironment by administering an effective amount of a compound of Formula (I).

  本公开提供了治疗癌症的方法，其中包括通过给予化合物Formula (I)的有效剂量来治疗癌症。在某些实施例中，癌症是实体癌。在某些实施例中，癌症是黑色素瘤。在某些方面，本公开提供了通过给予化合物Formula (I)的有效剂量来增加实体肿瘤微环境中CD8+ T细胞/CD4+ T细胞比率的方法。