m-methoxybenzylmercaptoacetic acid | 18926-47-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: m-methoxybenzylmercaptoacetic acid
• 英文别名: (3-Methoxy-benzylthio)-essigsaeure；2-([3-methoxyphenyl]methylthio)acetic acid；2-[(3-Methoxyphenyl)methylsulfanyl]acetic acid
• CAS: 18926-47-1
• 化学式: C₁₀H₁₂O₃S
• mdl: MFCD03086024
• 分子量: 212.269
• InChiKey: QMFCNAYBAHKUKR-UHFFFAOYSA-N

物化性质

• 熔点：
  95-96 °C
• 沸点：
  366.5±27.0 °C(Predicted)
• 密度：
  1.238±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  71.8
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2930909090

反应信息

• 作为反应物：
  描述：

  m-methoxybenzylmercaptoacetic acid 在 三氯乙酸酐 作用下， 以74%的产率得到7-methoxy-1H-2-benzothiopyran-4(3H)-one
  参考文献：
  名称：

  用三氯乙酸酐进行无溶剂傅-克环化

  摘要：

  摘要 使用 1.1 当量对环境无害的三氯乙酸酐作为唯一的试剂和溶剂，获得了 Friedel-Crafts 环化产物。所得的酮包括苯并噻吩、苯并噻喃、苯并恶英、二苯并噻菌、二苯并恶英和四氢萘酮。

  DOI：

  10.1080/00397910802663394
• 作为产物：
  描述：

  ethyl 2-((3-methoxybenzyl)thio)acetate 在 水 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 m-methoxybenzylmercaptoacetic acid
  参考文献：
  名称：

  Discovery of Novel 4-Arylisochromenes as Anticancer Agents Inhibiting Tubulin Polymerization

  摘要：

  XJP-L (8), a derivative of the natural product (+/-)-7,8-dihydroxy-3-methylisochroman-4-one isolated from the peel of Musa sapien turn L., was found to exhibit weak inhibitory activity of tubulin polymerization (IC50 = 10.6 mu M) in our previous studies. Thus, a series of 4-arylisochromene derivatives were prepared by incorporating the trimethoxyphenyl moiety into 8, among which compound (+/-)-19b was identified as the most potent compound with IC50 values ranging from 10 to 25 nM against a panel of cancer cell lines. Further mechanism studies demonstrated that (+/-)-19b disrupted the intracellular microtubule network, caused G2/M phase arrest, induced cell apoptosis, and depolarized mitochondria of K562 cells. Moreover, ()-19b exhibited potent in vitro antivascular and in vivo antitumor activities. Notably, the R-configured enantiomer of (+/-)-19b, which was prepared by chiral separation, was slightly more potent than (+/-)-19b and was much more potent than the S-configured enantiomer in both antiproliferative and antitubulin assays. Our findings suggest that (+/-)-19b deserves further research as a potential antitubulin agent for the treatment of cancers.

  DOI：

  10.1021/acsmedchemlett.8b00217

文献信息

• Design, Synthesis and Evaluation of 3-Substituted Coumarin Derivatives as Anti-inflammatory Agents
  作者：Tao Wang、Tao Peng、Xiaoxue Wen、Gang Wang、Shuchen Liu、Yunbo Sun、Shouguo Zhang、Lin Wang

  DOI：10.1248/cpb.c19-01085

  日期：2020.5.1

  Coumarin moiety has garnered momentous attention especially in the design of compounds with significant biological activities. In this work, a series of 3-substituted coumarin derivatives 6a-6l were synthesized and fully characterized. Most of the compounds could obviously inhibit the activity of cyclooxygenase-1 (COX-1) at the concentration of 10 µM. Besides, 6h and 6l exhibited highest inhibitory

  香豆素部分已经引起了广泛的关注，特别是在具有显着生物学活性的化合物的设计中。在这项工作中，合成并充分表征了一系列3-取代的香豆素衍生物6a-6l。在10 µM的浓度下，大多数化合物都能明显抑制环氧合酶1（COX-1）的活性。此外，6h和6l对COX-2的抑制作用最高，抑制率分别为33.48％和35.71％。还讨论了详细的结构-活性关系（SAR）。在体内研究中，6b，6i和6l可以以20 mg / kg的剂量显着抑制小鼠体内由二甲苯引起的耳肿。特别地，在10mg / kg的剂量下6l似乎是最有效的化合物，表现出与消炎痛相当的有利的抗炎活性。
• Solvent-Free Friedel–Crafts Cyclization with Trichloroacetic Anhydride
  作者：Ben Andrews、Kae Bullock、Shannon Condon、John Corona、Roman Davis、John Grimes、Andrew Hazelwood、Elie Tabet

  DOI：10.1080/00397910802663394

  日期：2009.7.7

  Abstract Friedel–Crafts cyclization products were obtained using 1.1 equivalents of environmentally benign trichloroacetic anhydride as sole reagent and solvent. The resulting ketones included benzothiepins, benzothiopyrans, benzoxepins, dibenzothiepins, dibenzoxepins, and tetralones.

  摘要 使用 1.1 当量对环境无害的三氯乙酸酐作为唯一的试剂和溶剂，获得了 Friedel-Crafts 环化产物。所得的酮包括苯并噻吩、苯并噻喃、苯并恶英、二苯并噻菌、二苯并恶英和四氢萘酮。
• [EN] BENZOPYRANOPYRAZOLYL DERIVATIVES FOR THE TREATMENT OF INFLAMMATION<br/>[FR] DERIVES DE BENZOPYRANOPYRAZOLYLE POUR LE TRAITEMENT DES INFLAMMATIONS
  申请人：G.D. SEARLE & CO.

  公开号：WO1996009304A1

  公开（公告）日：1996-03-28

  (EN) A class of benzopyranopyrazolyl derivatives is described for use in treating inflammation and inflammation-related disorders. Compounds of particular interest are defined by formula (I) wherein A is -(CH2)m-X-(CH2)n-; wherein X is S(O)p or O; wherein m is 0 or 1; wherein n is 0 or 1; wherein p is 0 or 1; wherein B is selected from phenyl and five and six membered heteroaryl; wherein R1 is selected from lower haloalkyl, cyano, lower hydroxyalkyl, formyl, lower alkoxycarbonyl, lower alkoxy, lower N-alkylaminocarbonyl, N-phenylaminocarbonyl, lower N,N-dialkylaminocarbonyl and lower N-alkyl-N-phenylaminocarbonyl; wherein R2 is phenyl substituted at a substitutable position with a radical selected from lower alkylsulfonyl and aminosulfonyl; and wherein R4 is one or more radicals selected from hydrido, halo, lower alkylthio, lower alkylsulfinyl, lower alkyl, cyano, carboxyl, lower alkoxycarbonyl, aminocarbonyl, lower haloalkyl, hydroxyl, lower alkoxy, amino, lower N-alkylamino, lower N,N-dialkylamino, lower hydroxyalkyl and lower haloalkoxy; or a pharmaceutically-acceptable salt thereof.(FR) L'invention concerne une classe de dérivés de benzopyranopyrazolyle destinés à être utilisés dans le traitement des inflammations et les troubles apparentés à une inflammation. Les composés présentant un intérêt particulier répondent à la formule (I) dans laquelle: A représente -(CH2)m -X-(CH2)n, où X représente S(Op) ou O, m vaut 0 ou 1, n vaut 0 ou 1, et p vaut 0 ou 1; B est choisi entre phényle et un groupe hétéroaryle à cinq ou six chaînons; R1 est choisi parmi haloalkyle inférieur, cyano, hydroxyalkyle inférieur, formyle, alcoxycarbonyle inférieur, alcoxy inférieur, N-alkylaminocarbonyl inférieur, N-phénylaminocarbonyle, N,N-dialkylaminocarbonyl inférieur et N-alkyl-N-phénylaminocarbonyl inférieur; R2 représente un phényle substitué dans une position de substitution par un radical choisi entre alkysulfonyle inférieur et aminosulfonyle; et R4 représente un ou plusieurs radicaux appartenant au groupe hybrido, halo, alkylthio inférieur, alkylsufinyle inférieur, alkyle inférieur, cyano, carboxyl, alcoxycarbonyl inférieur, aminocarbonyl, haloalkyle inférieur, hydroxyle, alcoxy inférieur, amino, N-alkylamino inférieur, N,N-dialkylamino inférieur, hydroxyalkyl inférieur et haloalcoxy inférieur. L'invention concerne également un sel pharmaceutiquement acceptable desdits dérivés.

  描述了一类苯并吡唑基衍生物，用于治疗炎症和与炎症相关的疾病。特别感兴趣的化合物由式(I)定义，其中A为-(CH2)m-X-(CH2)n-；其中X为S(O)p或O；其中m为0或1；其中n为0或1；其中p为0或1；其中B选自苯基和五元和六元杂环基；其中R1选自低卤代烷基、氰基、低羟基烷基、甲酰基、低烷氧羰基、低烷氧基、低N-烷基氨基羰基、N-苯基氨基羰基、低N,N-二烷基氨基羰基和低N-烷基-N-苯基氨基羰基；其中R2为苯基，在可取代位置上用从低烷基磺酰基和氨基磺酰基中选择的基团取代；其中R4为一个或多个从氢、卤素、低烷基硫基、低烷基亚磺酰基、低烷基、氰基、羧基、低烷氧羰基、氨基羰基、低卤代烷基、羟基、低烷氧基、氨基、低N-烷基氨基、低N,N-二烷基氨基、低羟基烷基和低卤代烷氧基中选择的基团；或其药学上可接受的盐。
• Cyclic pyrazoles for the inhibition of mitogen activated protein kinase-activated protein kinase-2
  申请人：Pharmacia Corporation

  公开号：US20040127492A1

  公开（公告）日：2004-07-01

  Cyclic pyrazole compounds are described which inhibit mitogen activated protein kinase-activated protein kinase-2 (MK-2). Methods of making such compounds are described, as well as a method of using them for the inhibition of MK-2 in a subject in need of such inhibition, where the method involves administering to the subject an MK-2 inhibiting compound of the present invention. Pharmaceutical compositions and kits which contain the present MK-2 inhibiting compounds are also described.

  本发明涉及一种环状吡唑化合物，其能够抑制丝裂原活化蛋白激酶激活蛋白激酶-2（MK-2）。本发明还描述了制备这种化合物的方法，以及一种使用它们来抑制需要这种抑制的受体的方法，其中该方法涉及向受体中注射本发明的MK-2抑制化合物。本发明还描述了包含本MK-2抑制化合物的药物组合物和工具箱。
• Benzopyranopyrazolyl derivatives for the treatment of inflammation
  申请人：——

  公开号：US05547975A1

  公开（公告）日：1996-08-20

  A class of benzopyranopyrazolyl derivatives is described for use in treating inflammation and inflammation-related disorders. Compounds of particular interest are defined by Formula I ##STR1## wherein A is --(CH.sub.2).sub.m --X--(CH.sub.2).sub.n --; wherein X is S(O).sub.p or O; wherein m is 0 or 1; wherein n is 0 or 1; wherein p is 0 or 1; wherein B is selected from phenyl and five and six membered heteroaryl; wherein R.sup.1 is selected from lower haloalkyl, cyano, formyl, lower alkoxycarbonyl, lower alkoxy, lower N-alkylaminocarbonyl, N-phenylaminocarbonyl, lower N,N-dialkylaminocarbonyl and lower N-alkyl-N-phenylaminocarbonyl; wherein R.sup.2 is phenyl substituted at a substitutable position with a radical selected from lower alkylsulfonyl and sulfamyl; and wherein R.sup.4 is one or more radicals selected from hydrido, halo, lower alkylthio, lower alkylsulfinyl, lower alkyl, cyano, carboxyl, lower alkoxycarbonyl, aminocarbonyl, lower haloalkyl, hydroxyl, lower alkoxy, amino, lower N-alkylamino, lower N,N-dialkylamino, lower hydroxyalkyl and lower haloalkoxy; or a pharmaceutically-acceptable salt thereof.

  本文介绍了一类苯并吡唑衍生物，用于治疗炎症和炎症相关疾病。特别感兴趣的化合物由式I定义，其中A为--(CH.sub.2).sub.m --X--(CH.sub.2).sub.n --；其中X为S(O).sub.p或O；其中m为0或1；其中n为0或1；其中p为0或1；其中B选自苯基和五元和六元杂环；其中R.sup.1选自较低的卤代烷基、氰基、甲酰基、较低的烷氧羰基、较低的烷氧基、较低的N-烷基氨基羰基、N-苯基氨基羰基、较低的N,N-二烷基氨基羰基和较低的N-烷基-N-苯基氨基羰基；其中R.sup.2是苯基，在可取代位置上取代有较低烷基磺酰基和磺酰胺基中的一种基团；其中R.sup.4是一个或多个基团，选自氢、卤、较低烷基硫基、较低烷基亚磺酰基、较低烷基、氰基、羧基、较低烷氧羰基、氨基羰基、较低卤代烷基、羟基、较低烷氧基、氨基、较低N-烷基氨基、较低N,N-二烷基氨基、较低羟基烷基和较低卤代羟基烷氧基；或其药学上可接受的盐。