2-[(pyridin-2-ylmethyl)thio]acetic acid | 21897-11-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-[(pyridin-2-ylmethyl)thio]acetic acid
• 英文别名: 2-(pyridin-2-ylmethylthio)acetic acid；pyridin-2-ylmethylsulfanyl-acetic acid；α--essigsaeure；2-[(Pyridin-2-ylmethyl)sulfanyl]acetic acid；2-(pyridin-2-ylmethylsulfanyl)acetic acid
• CAS: 21897-11-0
• 化学式: C₈H₉NO₂S
• mdl: MFCD02755443
• 分子量: 183.231
• InChiKey: HKUYJDRVSFQORH-UHFFFAOYSA-N

物化性质

• 熔点：
  136 °C
• 沸点：
  339.8±27.0 °C(Predicted)
• 密度：
  1.303±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  75.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[(pyridin-2-ylmethyl)thio]acetic acid 、 组胺 在 N,N'-羰基二咪唑 作用下， 生成 N-[2-(1H-Imidazol-4-yl)-ethyl]-2-(pyridin-2-ylmethylsulfanyl)-acetamide
  参考文献：
  名称：

  Acylated and alkylated histamine derivatives as new histamine H3-receptor antagonists

  摘要：

  New histamine H-3-receptor antagonists were prepared and investigated for their ability to increase synthesis and release of histamine mediated by inhibition of presynaptically located H-3-receptors. Acyl derivatives of histamine methylated at different positions show poor activity at H-3-receptors, whereas N-alpha-alkyl and particularly N-alpha-acyl derivatives of histamine possess moderate to good H-3-receptor antagonist activity. A not-too-bulky and lipophilic residue in an optimal distance of 3-4 methylene groups from the amide function leads to potent and selective H-3-receptor antagonists. N-alpha-Histamine-gamma-phenylbutyramide 11 and N-alpha-histamine-gamma-cyclohexylbutyramide 13 are H-3-receptor antagonists with -log K-i of 7.1 and 7.3, respectively. Structure-activity relationships of different substitution patterns are discussed.

  DOI：

  10.1016/0223-5234(94)90031-0
• 作为产物：
  描述：

  ethyl (2-picolylsulfenyl)acetate 在 sodium hydroxide 作用下， 反应 3.0h， 以96%的产率得到2-[(pyridin-2-ylmethyl)thio]acetic acid
  参考文献：
  名称：

  Octahedral rhodium(III) complexes as kinase inhibitors: Control of the relative stereochemistry with acyclic tridentate ligands

  摘要：

  Octahedral metal complexes are attractive structural templates for the design of enzyme inhibitors as has been demonstrated, for example, with the development of metallo-pyridocarbazoles as protein kinase inhibitors. The octahedral coordination sphere provides untapped structural opportunities but at the same time poses the drawback of dealing with a large number of stereoisomers. In order to address this challenge of controlling the relative metal-centered configuration, the synthesis of rhodium(III) pyridocarbazole complexes with facially coordinating acyclic tridentate ligands was investigated. A strategy for the rapid synthesis of such complexes is reported, the diastereoselectivities of these reactions were investigated, the structure of several complexes were determined by X-ray crystallography, the high kinetic stability of such complexes in thiol-containing solutions was demonstrated in H-1-NMR experiments, and the protein kinase inhibition ability of this class of complexes was confirmed. It can be concluded that the use of multidentate ligands is currently maybe the most practical strategy to avoid a large number of possible stereoisomers in the course of exploiting octahedral coordination spheres as structural templates for the design of bioactive molecules. (C) 2015 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.jinorgbio.2015.01.005

文献信息

• Investigation of the Coordination Interactions of S-(Pyridin-2-ylmethyl)-<scp>l</scp>-Cysteine Ligands with M(CO)₃⁺ (M = Re, ^99mTc)
  作者：Haiyang He、Jennifer E. Morley、Brendan Twamley、Ryan H. Groeneman、Dejan-Krešimir Buč̌ar、Leonard R. MacGillivray、Paul D. Benny

  DOI：10.1021/ic901159r

  日期：2009.11.16

  Development of new ligands for fac-M(OH2)3(CO)3+ (M = Re, 99mTc) led the investigation with S-(pyridin-2-ylmethyl)-l-cysteine, 1. The ligand 1 has potential to coordinate with the metal through three different tridentate modes: tripodal through cysteine (O,N,S) and two linear involving the S-pyridyl and cysteine (O,S,NPy, N,S,NPy). From the reaction with 1, two species were observed in the 1H NMR,

  fac -M（OH 2）3（CO）3 +（M = Re，99m Tc）的新配体的开发带动了S-（吡啶-2-基甲基）-1-半胱氨酸1的研究。配体1具有通过三种不同的三齿模式与金属配位的潜力：三脚架通过半胱氨酸（O，N，S）和两个涉及S-吡啶基和半胱氨酸的线性（O，S，N Py，N，S，N Py）。从与反应1中，观察到两个种类1 H NMR，其中初级产物是线性FAC -Re（N，S，N PY -1）（CO）3 +，2a，复杂的。为了确定次要产物的配位模式，从S-（吡啶-2-基甲基）-Boc - 1-半胱氨酸甲酯制备了1的官能化类似物3，在C末端带有正交保护基（甲酯） S-（吡啶-2-基甲基）-1-半胱氨酸甲酯4或N-末端（Boc）在S-（吡啶-2-基甲基）-Boc- 1-半胱氨酸6中，专门指导配位模式的FAC -M（H 2 O）3（CO）3 +要么N，S，N PY或O，S，N Py。观察到两个非对映异构体[
• Cyclometalated phenylquinoline rhodium complexes as protein kinase inhibitors
  作者：Stefan Mollin、Sebastian Blanck、Klaus Harms、Eric Meggers

  DOI：10.1016/j.ica.2012.04.035

  日期：2012.12

  A new metal-containing scaffold for the generation of rhodium(III)-based protein kinase inhibitors is introduced in which the pharmacophore ligand 4-phenylpyrrolo[3,4-c]quinoline-1,3(2H)-dione is designed to form two hydrogen bonds with the hinge region of the ATP-binding site. The phenylquinoline ligand binds to rhodium(III) in a cyclometalated fashion by coordinating to the quinoline nitrogen and forming a covalent bond to a carbon atom of the phenyl substituent. Additional acyclic tridentate ligands were used to control the relative stereochemistry, whereas a chiral proline-derived tridentate ligand was employed for the asymmetric synthesis of single enantiomers. Finally, protein kinase profiling and inhibition data confirmed that the new rhodium(III)-phenylquinoline scaffold is suitable for the generation of selective protein kinase inhibitors. (C) 2012 Elsevier B.V. All rights reserved.
• SEKINE, YASUO;HIRAKAWA, NOBUHIRO;KASHIWABA, NORIAKI;YAMAURA, TETSUAKI;HAR+
  作者：SEKINE, YASUO、HIRAKAWA, NOBUHIRO、KASHIWABA, NORIAKI、YAMAURA, TETSUAKI、HAR+

  DOI：——

  日期：——
• 11BETA-LANGKETTIG-SUBSTITUIERTE ESTRATRIENE, VERFAHREN ZUR HERSTELLUNG, PHARMAZEUTISCHE PRÄPARATE, DIE DIESE 11BETA-LANGKETTIG-SUBSTITUIERTEN ESTRATRIENE ENTHALTEN, SOWIE DEREN VERWENDUNG ZUR HERSTELLUNG VON ARZNEIMITTELN
  申请人：Schering Aktiengesellschaft

  公开号：EP1187846A2

  公开（公告）日：2002-03-20
• US4772683A
  申请人：——

  公开号：US4772683A

  公开（公告）日：1988-09-20