5-oxo-1,4-thiazepane-3-carboxylic acid | 35082-57-6

• 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: 5-oxo-1,4-thiazepane-3-carboxylic acid
• 英文别名: (R)-5-oxo-1,4-thiazepane-3-carboxylic acid；(R)-5-Oxo-1,4-thiazepane-3-carboxylic acid；(3R)-5-oxo-1,4-thiazepane-3-carboxylic acid
• CAS: 35082-57-6
• 化学式: C₆H₉NO₃S
• 分子量: 175.208
• InChiKey: JICTZUFURQRLDW-BYPYZUCNSA-N

物化性质

• 沸点：
  512.1±50.0 °C(Predicted)
• 密度：
  1.364±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  91.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-oxo-1,4-thiazepane-3-carboxylic acid 、 3,5-二氯苯胺 在 1-羟基苯并三唑 、 N,N'-二异丙基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 (3R)-N-(3,5-dichlorophenyl)-5-oxo-1,4-thiazepane-3-carboxamide
  参考文献：
  名称：

  Discovery and optimization of a novel CNS penetrant series of mGlu4 PAMs based on a 1,4-thiazepane core with in vivo efficacy in a preclinical Parkinsonian model

  摘要：

  DOI：

  10.1016/j.bmcl.2021.127838
• 作为产物：
  描述：

  S-(2-Methoxycarbonyl-aethyl)-L-cystein 在 氨 作用下， 以 甲醇 为溶剂， 反应 168.0h， 以13%的产率得到5-oxo-1,4-thiazepane-3-carboxylic acid
  参考文献：
  名称：

  Discovery and optimization of a novel CNS penetrant series of mGlu4 PAMs based on a 1,4-thiazepane core with in vivo efficacy in a preclinical Parkinsonian model

  摘要：

  DOI：

  10.1016/j.bmcl.2021.127838

文献信息

• A novel near-infrared fluorescent probe based on isophorone for the bioassay of endogenous cysteine
  作者：Hong-Bo Liu、Hai Xu、Xin Guo、Jian Xiao、Zheng-Hong Cai、Ya-Wen Wang、Yu Peng

  DOI：10.1039/d0ob02405h

  日期：——

  solution with a large Stokes shift (143 nm). The detection limit of Cys was 1.23 μM, which was lower than that of the intracellular Cys concentration. DDP was cell membrane-permeable and had been successfully applied to the detection of intracellular Cys in HeLa cells. The detection mechanism was determined by 1H NMR titration, MS and DFT calculations.

  合成了双氰基异佛尔酮/丙烯酸酯组合探针（DDP），并将其设计为近红外（NIR）荧光传感器，用于在斯托克斯位移（143 nm）大的水溶液中通过Hcy和GSH快速鉴定Cys。Cys的检测限为1.23μM，低于细胞内Cys的浓度。DDP可透过细胞膜，并已成功应用于HeLa细胞中胞内Cys的检测。通过1 H NMR滴定，MS和DFT计算确定检测机理。
• Reaction‐Based Europium Complex for Specific Detection of Cysteine Over Homocysteine and Glutathione with Variable‐Temperature Kinetic Studies
  作者：Yuk‐Wang Yip、Zhiyuan Yan、Ga‐Lai Law、Wing‐Tak Wong

  DOI：10.1002/ejic.201801315

  日期：2019.2.14

  A water‐soluble europium(III)‐based probe, EuL, has been designed and synthesized for selective recognition of cysteine (Cys) over other structurally similar thiols and amino derivatives due to formation of a more stable and preferable seven‐membered ring. Addition of Cys shows a significant response with quenching of over 90 % of the initial signal (Hcys: 10.5 %, GSH: 3.6 % respectively). A good linear

  设计并合成了一种基于水溶性euro（III）的探针EuL，以选择性识别半胱氨酸（Cys），从而形成了更稳定且更佳的七元环，从而取代了其他结构相似的硫醇和氨基衍生物。Cys的添加显示出显着的响应，淬灭了超过原始信号的90％（Hcys：分别为10.5％，GSH：3.6％）。发射强度与Cys浓度之间建立了良好的线性相关性。
• A novel and effective benzo[<i>d</i>]thiazole-based fluorescent probe with dual recognition factors for highly sensitive and selective imaging of cysteine <i>in vitro</i> and <i>in vivo</i>
  作者：Meiqing Zhu、Xiaoqin Wu、Linfeng Sang、Fugang Fan、Lijun Wang、Xiangwei Wu、Rimao Hua、Yi Wang、Qing X. Li

  DOI：10.1039/c9nj03202a

  日期：——

  Double recognition groups significantly improved the selectivity of a fluorescent probe to Cys in living cells.

  双重识别基团显著提高了荧光探针在活细胞中对半胱氨酸的选择性。
• A New Endoplasmic Reticulum (ER)-Targeting Fluorescent Probe for the Imaging of Cysteine in Living Cells
  作者：Lei Zhou、Yunxia Li、Aiqin Zhou、Guanghui Zhang、Zhi-Qiang Cheng、Yong-Xi Ge、Shan-Kui Liu、Ricardo Bentes Azevedo、Juan Zhang、Shenglin Jiang、Cheng-Shi Jiang

  DOI：10.1007/s10895-020-02615-x

  日期：2020.12

  Cysteine (Cys) is an important endogenous amino acid and plays critical physiological roles in living systems. Herein, an endoplasmic reticulum (ER)-targeting fluorescent probe (FER-Cys) was designed and prepared for imaging of Cys in living cells. The probe FER-Cys consists of a fluorescein framework as the fluorescent platform, acrylate group as the response site for the selective recognition of Cys, and

  半胱氨酸（Cys）是重要的内源氨基酸，在生命系统中起着至关重要的生理作用。在此，设计并准备了靶向内质网（ER）的荧光探针（FER-Cys）以对活细胞中的Cys成像。探针FER-Cys由荧光素框架作为荧光平台，丙烯酸酯基作为选择性识别Cys的反应位点和ER特异性对甲苯磺酰胺片段组成。探针FER-Cys对Cys响应后，可以明显检测到546 nm处的开启荧光信号。探针FER-Cys进一步显示出对Cys的理想选择性。最后，探针FER-Cys被证明可以选择性地检测活细胞中的Cys，并成功地在H 2 O 2引起的氧化还原失衡的细胞模型中成像Cys水平的变化。
• Conjugate Addition/Cyclization Sequence Enables Selective and Simultaneous Fluorescence Detection of Cysteine and Homocysteine
  作者：Xiaofeng Yang、Yixing Guo、Robert M. Strongin

  DOI：10.1002/anie.201103759

  日期：2011.11.4

  Similar but different: A benzothiazole derivative can be used to detect cysteine (Cys) and homocysteine (Hcy) simultaneously in neutral media. The method involves thioether formation followed by cyclization to release 2‐(2′‐hydroxy‐3′‐methoxyphenyl)benzothiazole (HMBT) and a lactam. The differences in ring‐formation kinetics allow spectral or kinetic modes to be used to identify Cys and Hcy.

  相似但不同：苯并噻唑衍生物可用于在中性介质中同时检测半胱氨酸 (Cys) 和同型半胱氨酸 (Hcy)。该方法涉及硫醚形成，然后环化释放 2-(2'-羟基-3'-甲氧基苯基)苯并噻唑 (HMBT) 和内酰胺。成环动力学的差异允许使用光谱或动力学模式来识别 Cys 和 Hcy。