5-chloro-2-(methylsulfanyl)benzoic acid | 62176-39-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-chloro-2-(methylsulfanyl)benzoic acid
• 英文别名: 2-Methylthio-5-chlorbenzoesaeure；5-Chlor-2-methylmercapto-benzoesaeure；S-Methyl-5-chlor-thiosalicylsaeure；5-chloro-2-methylsulfanylbenzoic acid
• CAS: 62176-39-0
• 化学式: C₈H₇ClO₂S
• 分子量: 202.661
• InChiKey: DHFONUYVBAIUFH-UHFFFAOYSA-N

物化性质

• 熔点：
  184-185 °C
• 沸点：
  324.3±32.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-chloro-2-(methylsulfanyl)benzoic acid 在 盐酸 作用下， 生成 4-氯茴香硫醚
  参考文献：
  名称：

  Brand; Groebe, Journal fur praktische Chemie (Leipzig 1954), 1924, vol. <2> 108, p. 12

  摘要：

  DOI：
• 作为产物：
  描述：

  在 copper(I) oxide 、 盐酸 、 sodium nitrite 作用下， 生成 5-chloro-2-(methylsulfanyl)benzoic acid
  参考文献：
  名称：

  邻近族群参与硫化物与氯胺-t的反应

  摘要：

  研究了氯胺-T与邻位取代的芳基甲基硫化物和二芳基硫化物反应中的邻近基团。该反应显着地通过的空间位阻效应阻碍了邻苯基环的取代基，但有一个CO基部分示出了在按下列顺序的邻位效果：ö -CH 2 CO 2我〜ö -CH 2 CO 2 H ^ < ö -CH 2 CO 2 - < ö -CO 2我〜ö -CO 2 ħ< ö -CO 2 -根据盐和同位素效应，可以排除速率确定步骤中的2o-CO 2。具有相邻基团参与的取代基降低了在含有水的溶剂中亚砜亚胺的收率。TsNHCl进行的硫化物的亲电氯化反应可以认为是决定速率的步骤，其中带正电的sulph中心通过过渡态的带负电或带羰基的氧稳定。这种类型的相互作用在快速的产物控制步骤中阻碍了磺酰胺离子在the中心的亲核攻击，从而降低了亚砜亚胺的收率。

  DOI：

  10.1016/0040-4020(78)88417-8

文献信息

• Benzisothiazol-3-ones through a Metal-Free Intramolecular N-S Bond Formation
  作者：Ke Yang、Hao Zhang、Ben Niu、Tiandi Tang、Haibo Ge

  DOI：10.1002/ejoc.201801090

  日期：2018.11.1

  An efficient selectfluor‐promoted synthesis of benzoisothiazol‐3‐ones through a sequential N–S bond formation and C–S bond cleavage process was developed.

  通过连续的N–S键形成和C–S键裂解过程，开发了一种有效的由Selectfluor促进的苯并异噻唑-3-酮的合成方法。
• N-alkyl-2-phenoxyethanamines, their preparation and use
  申请人：The Trustees of Columbia University In the City of New York

  公开号：US10570148B2

  公开（公告）日：2020-02-25

  The present invention provides a compound having the structure: (structurally represented) wherein R1, R2, R3, R4, and R5 are each independently H, halogen, CF3 or C1-C4 alkyl; R6 is alkyl; A is absent or present, and when present is —C(O)— or —C(O)NH—; B is substituted or unsubstituted monocycle, bicycle, heteromonocycle, heterobicycle, benzyl, CO2H or (C1-C4 alkyl)-CO2H, wherein when B is CO2H, then A is present and is —C(O)—, or a pharmaceutically acceptable salt thereof.

  本发明提供了一种具有以下结构的化合物：(结构表示），其中 R1、R2、R3、R4 和 R5 各自独立地为 H、卤素、CF3 或 C1-C4 烷基；R6 为烷基；A 不存在或存在，存在时为 -C(O)- 或 -C(O)NH- ；B 为取代或未取代的单环、单车、杂单环、杂单车、苄基、CO2H 或 (C1-C4 烷基)-CO2H，其中当 B 为 CO2H 时，则 A 存在且为 -C(O)-，或其药学上可接受的盐。
• Aziridinyldinitrobenzamides:  Synthesis and Structure−Activity Relationships for Activation by <i>E. </i><i>coli</i> Nitroreductase
  作者：Nuala A. Helsby、Graham J. Atwell、Shangjin Yang、Brian D. Palmer、Robert F. Anderson、Susan M. Pullen、Dianne M. Ferry、Alison Hogg、William R. Wilson、William A. Denny

  DOI：10.1021/jm0498699

  日期：2004.6.1

  The 5-aziridinyl-2,4-dinitrobenzamide CB 1954 is a substrate for the oxygen-insensitive nitroreductase (NTR) from E. coli and is in clinical trial in combination with NTR-armed adenoviral vectors in a GDEPT protocol; CB 1954 is also of interest for selective deletion of NTR-marked cells in normal tissues. Since little further drug development has been carried out around this lead, we report here the synthesis of more soluble variants and regioisomers and structure-activity relationship (SAR) studies. The compounds were primarily prepared from the corresponding chloro(di)nitroacids through amide side chain elaboration and subsequent aziridine formation. One-electron reduction potentials [E(1)], determined by pulse radiolysis, were around -400 mV, varying little for aziridinyldinitrobenzamide regioisomers. Cytotoxicity in a panel of NTR-transfected cell lines showed that in the CB 1954 series there was considerable tolerance of substituted CONHR side chains. The isomeric 2-aziridinyl-3,5-dinitrobenzamide was also selective toward NTR+ve lines but was approximately 10-fold less potent than CB 1954. Other regioisomers were too insoluble to evaluate. While CB 1954 gave both 2- and 4-hydroxylamine metabolites in NTR+ve cells, related analogues with substituted carboxamides gave only a single hydroxylamine metabolite possibly because the steric bulk in the side chain constrains binding within the active site. CB 1954 is also a substrate for the two-electron reductase DT-diaphorase, but all of the other aziridines (regioisomers and close analogues) were poorer substrates with resulting improved specificity for NTR. Bystander effects were determined in multicellular layer cocultures and showed that the more hydrophilic side chains resulted in a modest reduction in bystander killing efficiency. A limited number of analogues were tested for in vivo activity, using a single ip dose to CD-1 nude mice bearing WiDr-NTRneo tumors. The most active of the CB 1954 analogues was a diol derivative, which showed a substantial median tumor growth delay (59 days compared with >85 days for CB 1954) in WiDr xenografts comprising 50% NTR+ve cells. The diol is much more soluble and can be formulated in saline for administration. The results suggest there may be advantages with carefully selected analogues of CB 1954; the weaker bystander effect of its diol derivative may be an advantage in the selective cell ablation of NTR-tagged cells in normal tissues.
• Ruff, Ferenc; Kucsman, Arpad, Journal of the Chemical Society. Perkin transactions II, 1985, p. 683 - 688
  作者：Ruff, Ferenc、Kucsman, Arpad

  DOI：——

  日期：——
• N-ALKYL-2-PHENOXYETHANAMINES, THEIR PREPARATION AND USE
  申请人：Petrukhin Konstantin

  公开号：US20180222919A1

  公开（公告）日：2018-08-09

  The present invention provides a compound having the structure: (structurally represented) wherein R1, R2, R3, R4, and R5 are each independently H, halogen, CF3 or C1-C4 alkyl; R6 is alkyl; A is absent or present, and when present is —C(O)— or —C(O)NH—; B is substituted or unsubstituted monocycle, bicycle, heteromonocycle, heterobicycle, benzyl, CO2H or (C1-C4 alkyl)-CO2H, wherein when B is CO2H, then A is present and is —C(O)—, or a pharmaceutically acceptable salt thereof.