乙基2-[(1S)-1-氨基乙基]-1,3-噻唑-4-羧酸酯 | 216480-96-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 乙基2-[(1S)-1-氨基乙基]-1,3-噻唑-4-羧酸酯
• 英文名称: (S)-ethyl 2-(1-acetamidoethyl)thiazole-4-carboxylate
• 英文别名: NH2-Ala-thioazole-OEt；EtO-Thiazole-Ala-NH2；(S)-Ethyl 2-(1-aminoethyl)thiazole-4-carboxylate；ethyl 2-[(1S)-1-aminoethyl]-1,3-thiazole-4-carboxylate
• CAS: 216480-96-5
• 化学式: C₈H₁₂N₂O₂S
• 分子量: 200.261
• InChiKey: BIHAKLFZRIHNNM-YFKPBYRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  93.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  乙基2-[(1S)-1-氨基乙基]-1,3-噻唑-4-羧酸酯 在 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 苯甲醚 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.75h， 生成 NH2-Val-Ala-thioazole-OEt
  参考文献：
  名称：

  反式，反式Sanguinamide B和构象异构体的全合成

  摘要：

  报道了通过有效的合成策略制备的血红素酰胺B的第一个全合成。天然产物，反式，反式- Sanguinamide B（1），在具有热力学率，生成了反式，顺式-Sanguinamide B（2）和顺式，顺式- Sanguinamide B（3）。顺式，顺式Sanguinamide B构象异构体（3）完全转化为天然产物（1）和反式，顺式构象异构体（2）完全转化通过加热到170°C达到）。生物学评估表明，Sanguinamide B构象异构体破坏了铜绿假单胞菌中一种毒性决定簇的活性。

  DOI：

  10.1021/ol203290n
• 作为产物：
  描述：

  3-溴丙酮酸乙酯 在 吡啶 、 potassium hydrogencarbonate 、 三氟乙酸 、 三氟乙酸酐 作用下， 以 乙二醇二甲醚 、 苯甲醚 为溶剂， 反应 0.02h， 生成 乙基2-[(1S)-1-氨基乙基]-1,3-噻唑-4-羧酸酯
  参考文献：
  名称：

  Synthesis and Antimicrobial Activity in Vitro of New Amino Acids and Peptides Containing Thiazole and Oxazole Moieties

  摘要：

  2-(Pyrrolidinyl)thiazole-4-carboxylic acid 5d, 2-(1-aminoalkyl)thiazole-4-carboxamides and hydrazides 8, 10 have been synthesized using alanine, valine, and proline as educts. In addition oxazole amino acids derived from leucine 20a and alanine 20b and some peptides 13, 14, 16 containing the 5-ring heterocyclic backbone modifications have been prepared. The thiazole and oxazole containing amino acids and peptides showed moderate antibacterial activity in vitro against various Gram-positive (Staphylococcus aureus, Bacillus cereus, etc.) and Gram-negative (Escherichia coli, Proteus vulgar is, etc.) bacteria, fungi (Candida albicans), and yeast (Saccharomyces cerevisae, etc.).

  DOI：

  10.1002/(sici)1521-4184(19999)332:9<297::aid-ardp297>3.0.co;2-#

文献信息

• Synthesis of dolastatin I, a cytotoxic cyclic hexapeptide from the sea hare Dolabella auricularia
  作者：Hideo Kigoshi、Shiho Yamada

  DOI：10.1016/s0040-4020(99)00729-2

  日期：1999.10

  Dolastatin I, a cytotoxic cyclic hexapeptide isolated from the Japanese sea hare Dolabella auricularia, was enantioselectively synthesized, which confirmed its stereostructure.

  从日本海兔Dolabella auricularia分离出的细胞毒性环六肽Dolastatin I是对映选择性合成的，证实了其立体结构。
• The first synthesis of promothiocin A
  作者：Christopher J. Moody、Mark C. Bagley

  DOI：10.1039/a805762a

  日期：——

  The first total synthesis of the naturally occurring macrocyclic thiopeptide promothiocin A 1 is described.

  描述了天然存在的大环硫肽promothiocin A 1 的首次全合成。
• Synthesis, Structure–Activity Analysis, and Biological Evaluation of Sanguinamide B Analogues
  作者：Hendra Wahyudi、Worawan Tantisantisom、Xuechao Liu、Deborah M. Ramsey、Erinprit K. Singh、Shelli R. McAlpine

  DOI：10.1021/jo3017499

  日期：2012.12.7

  We report the first synthesis of sanguinamide B analogues. Substituting N-methylated (N-Me) amino acids, glycine (Gly), and L- or D-phenylalanine (Phe) into the backbone of sanguinamide B showed that only L- and D-Phe residues controlled the macrocycle conformation. The N-methylated and glycine analogues all had multiple conformations, whereas the L- and D-Phe derivatives only had a single conformation. Testing of all conformer analogues showed that inclusion of an L- or D-Phe was a superior design element than incorporating the N-Me moiety that is often utilized to control macrocyclic conformation. Finally, we show that there is an ideal Phe residue (in this case L-Phe) for generating compounds that have the greatest inhibitory effect on bacterial motility. Our data support the hypothesis that the macrocyclic conformation is dictated by the benzyl moiety requiring a "pseudoequatorial" position, and all other energy considerations are secondary.
• Sanguinamide B analogs: identification of active macrocyclic structures
  作者：Hendra Wahyudi、Worawan Tantisantisom、Shelli R. McAlpine

  DOI：10.1016/j.tetlet.2014.02.106

  日期：2014.4

  We report the synthesis of three new sanguinamide B (San B) analogs. We substituted in amino acids along the San B backbone with an N-Me, glycine, or an aromatic moiety (Phe or D-Phe) generating twelve derivatives in total. Testing in HCT-116 colon cancer cell lines resulted in establishing a structure-activity relationship. Our data show that the substitution of L- or D-Phe adjacent to the thiazole in the San B backbone locks the macrocycle into a single conformer, but only D-Phe analogs are cytotoxic. We demonstrate that the conformation of the macrocycle is extremely sensitive to stereochemistry and amino acid placement. (C) 2014 Elsevier Ltd. All rights reserved.
• Total syntheses of bacillamide C and neobacillamide A; revision of their absolute configurations
  作者：Verónica Martínez、Danilo Davyt

  DOI：10.1016/j.tetasy.2013.11.001

  日期：2013.12

  The enantiospecific syntheses of both enantiomers of bacillamide C and neobacillamide A are described, along with the measurement of their optical activities, leading to the revision of the proposed absolute configurations of these natural products. (C) 2013 Elsevier Ltd. All rights reserved.