N-(2,4-dichlorophenyl)glycine | 13370-65-5

• 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-(2,4-dichlorophenyl)glycine
• 英文别名: (2,4-dichlorophenyl) glycine；2,4-Dichlor-phenylglycin；N-(2,4-Dichlor-phenyl)-glycin；2-(2,4-dichloroanilino)acetic acid
• CAS: 13370-65-5
• 化学式: C₈H₇Cl₂NO₂
• 分子量: 220.055
• InChiKey: LTMPEYZFRFPAMX-UHFFFAOYSA-N

物化性质

• 熔点：
  138-140 °C
• 沸点：
  435.3±35.0 °C(Predicted)
• 密度：
  1.528±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(2,4-dichlorophenyl)glycine 在 乙酸酐 、 sodium nitrite 作用下， 以 二氯甲烷 为溶剂， 反应 7.8h， 以91%的产率得到3-(2,4-Dichlorophenyl)-1,2,3-oxadiazol-3-ium-5-olate
  参考文献：
  名称：

  中性条件下，在 NaNO2/Ac2O 存在下，双氯-1,4-二氮杂双环[2.2.2]辛烷络合物 (Cl2-DABCO) 有效促进 N-芳基甘氨酸一锅法转化为 Sydones

  摘要：

  Bis-chlorine-1,4-diazabicyclo[2.2.2]octane complex, (Cl 2 -DABCO) 被发现是一种活性氯络合物，可有效地将各种 N-芳基甘氨酸一锅法转化为高收率 (85 -95%) 在温和和中性条件下。

  DOI：

  10.3987/com-07-11033
• 作为产物：
  描述：

  <2,4-Dichlor-phenyl>-acetonitril 在 sodium hydroxide 作用下， 生成 N-(2,4-dichlorophenyl)glycine
  参考文献：
  名称：

  Synthesis of Ring-Substituted N-Phenylglycines, Their Nitriles and Amides

  摘要：

  DOI：

  10.1021/jo01360a028

文献信息

• Inhibitors of cathepsin S
  申请人：IRM LLC

  公开号：US20040198780A1

  公开（公告）日：2004-10-07

  The present invention provides compounds, compositions and methods for the selective inhibition of cathepsin S. In a preferred aspect, cathepsin S is selectively inhibited in the presence of at least one other cathepsin isozyme (e.g., cathespin K). The present invention also provides methods for treating a disease state in a subject by selectively inhibiting cathepsin S.

  本发明提供了用于选择性抑制蛋白酶S的化合物、组合物和方法。在一个优选方面，当至少存在另一种蛋白酶同工酶（例如，蛋白酶K）时，选择性地抑制蛋白酶S。本发明还提供了通过选择性抑制蛋白酶S来治疗受试者疾病状态的方法。
• Structure-activity relationships and mechanistic studies of novel mitochondria-targeted, leishmanicidal derivatives of the 4-aminostyrylquinoline scaffold
  作者：Matteo Staderini、Marta Piquero、María Ángeles Abengózar、Montserrat Nachér-Vázquez、Giulia Romanelli、Pilar López-Alvarado、Luis Rivas、Maria Laura Bolognesi、J. Carlos Menéndez

  DOI：10.1016/j.ejmech.2019.03.007

  日期：2019.6

  A new class of quinoline derivatives, bearing amino chains at C-4 and a styryl group at C-2, were tested on Leishmania donovani promastigotes and axenic and intracellular Leishmania pifanoi amastigotes. The introduction of the C-4 substituent improves the activity, which is due to interference with the mitochondrial activity of the parasite and its concomitant bioenergetic collapse by ATP exhaustion

  在Leishmania donovani promastigotes以及轴突和胞内Leishmania pifanoi amastigotes上测试了一类新的喹啉衍生物，它们在C-4处带有氨基链，在C-2上具有一个苯乙烯基。C-4取代基的引入提高了活性，这是由于干扰了该寄生虫的线粒体活性及其伴随的ATP耗尽所引起的生物能崩溃。某些化合物显示出令人满怀希望的抗疟药谱，对前鞭毛体和鞭毛体形式的微摩尔或亚微摩尔活性低，且选择性指数高。
• Discovery, synthesis and biological characterization of a series of <i>N</i>-(1-(1,1-dioxidotetrahydrothiophen-3-yl)-3-methyl-1<i>H</i>-pyrazol-5-yl)acetamide ethers as novel GIRK1/2 potassium channel activators
  作者：Swagat Sharma、Lauren Lesiak、Christopher D. Aretz、Yu Du、Sushil Kumar、Nagsen Gautam、Yazen Alnouti、Nikilesh V. Dhuria、Yashpal S. Chhonker、C. David Weaver、Corey R. Hopkins

  DOI：10.1039/d1md00129a

  日期：——

  The present study describes the discovery and characterization of a series of N-(1-(1,1-dioxidotetrahydrothiophen-3-yl)-3-methyl-1H-pyrazol-5-yl)acetamide ethers as G protein-gated inwardly-rectifying potassium (GIRK) channel activators. From our previous lead optimization efforts, we have identified a new ether-based scaffold and paired this with a novel sulfone-based head group to identify a potent

  本研究描述了一系列N -(1-(1,1-二氧化四氢噻吩-3-基)-3-甲基-1 H-吡唑-5-基)乙酰胺醚作为 G 蛋白内门控的发现和表征-整流钾（GIRK）通道激活剂。从我们之前的先导化合物优化工作中，我们已经确定了一种新的基于醚的支架，并将其与一种新型的基于砜的头基配对，以确定一种有效且选择性的 GIRK1/2 激活剂。此外，我们在第 1 层 DMPK 测定中评估了这些化合物，并确定了作为 GIRK1/2 激活剂显示纳摩尔效力的化合物，与典型的基于尿素的化合物相比，其代谢稳定性得到了改善。
• Process for producing optically active alpha-amino acid and optically active alpha-amino acid amine
  申请人：——

  公开号：US20030171597A1

  公开（公告）日：2003-09-11

  The present invention provides a process for efficiently producing an optically active &agr;-amino acid and an optically active &agr;-amino acid amide. After contacting with cells or processed cells thereof having an ability to asymmetrically hydrolyse, a water solvent is substituted with at least one solvent selected from the group consisting of linear, branched, or cyclic alcohol having 3 or more carbon atoms and the optically active &agr;-amino acid is preferentially precipitated from the alcohol solution. The addition of basic compounds, particularly potassium compounds to the alcohol solution containing the optically active &agr;-amino acid amide, which is obtained after the separation of the optically active &agr;-amino acid, enables the purification of the amide without the inclusion of amino acid into amino acid amide. Thus, the amide is subjected to the step of racemization and then recycled.

  本发明提供了一种高效生产光学活性α-氨基酸和光学活性α-氨基酸酰胺的方法。与具有不对称水解能力的细胞或经处理的细胞接触后，用至少一种来自直链、支链或环状醇中选择的溶剂替代水溶剂，并使光学活性α-氨基酸优先从醇溶液中沉淀。将碱性化合物，特别是钾化合物加入到含有光学活性α-氨基酸酰胺的醇溶液中，该酰胺在分离光学活性α-氨基酸后获得，使酰胺能够在不包括氨基酸转化为氨基酸酰胺的情况下纯化。因此，酰胺经过消旋步骤后再进行回收利用。
• Catalytic Activity of 1,3-Dibromo-5,5-dimethylhydantoin (DBH) in the One-Pot Transformation of<i>N</i>-Arylglycines to<i>N</i>-Arylsydnones in the Presence of NaNO₂/Ac₂O under Neutral Conditions: Subsequent Bromination of these Sydnones to their 4-Bromo Derivatives
  作者：Davood Azarifar、Hassan Ghasemnejad-Bosra

  DOI：10.1055/s-2006-926380

  日期：——

  1,3-Dibromo-5,5-dimethylhydantoin (DBH) has been found to efficiently catalyze the one-pot conversion of various N-arylglycines through N-nitrosation and cyclization to sydnones in combination with NaNO2 and Ac2O in high yields (80-94%) under mild and neutral conditions. Also, it was shown that DBH can conveniently­ promote the bromination of these sydnones to their 4-bromo substituted congeners in excellent yields in DMF at room temperature.

  研究发现，在温和的中性条件下，1,3-二溴-5,5-二甲基海因（DBH）可与 NaNO2 和 Ac2O 结合，高效催化各种 N-芳基甘氨酸通过 N-亚硝基化和环化反应一锅转化为茚酮类化合物，收率高达 80-94%。此外，研究还表明，DBH 可以方便地促进这些茚酮在室温下于 DMF 中溴化成其 4-溴取代的同系物，收率极高。