(3-甲氧苄基)甲基砜 | 25195-41-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: (3-甲氧苄基)甲基砜
• 英文名称: m-<(Methylsulfonyl)-methyl>-anisole
• 英文别名: 3-methoxybenzylmethylsulfon；(3-methoxybenzyl)methylsulfone；1-(Methanesulfonylmethyl)-3-methoxybenzene；1-methoxy-3-(methylsulfonylmethyl)benzene
• CAS: 25195-41-9
• 化学式: C₉H₁₂O₃S
• mdl: MFCD28127704
• 分子量: 200.258
• InChiKey: SPCZMGFOFSXHMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3-甲氧苄基)甲基砜 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 3-((methylsulfonyl)methyl)phenol
  参考文献：
  名称：

  Discovery of a Potent and Selective Sphingosine Kinase 1 Inhibitor through the Molecular Combination of Chemotype-Distinct Screening Hits

  摘要：

  Sphingosine kinase (SphK) is the major source of the lipid mediator and G protein-coupled receptor agonist sphingosine-l-phosphate (S1P). SIP promotes cell growth, survival, and migration and is a key regulator of lymphocyte trafficking. Inhibition of SIP signaling has been proposed as a strategy for treatment of inflammatory diseases and cancer. Two different formats of an enzyme-based high-throughput screen yielded two attractive chemotypes capable of inhibiting SO formation in cells. The molecular combination of these screening hits led to compound 22a (PF-543) with 2 orders of magnitude improved potency. Compound 22a inhibited SphK1 with an IC50 of 2 nM and was more than 100-fold selective for SphK1 over the SphK2 isoform. Through the modification of tail-region substituents, the specificity of inhibition for SphK1 and SphK2 could be modulated, yielding SphK1-selective, potent SphK1/2 dual, or SphK2-preferential inhibitors.

  DOI：

  10.1021/acs.jmedchem.7b00070
• 作为产物：
  描述：

  sodium methansulfinate 、 3-甲氧基溴苄 以 乙醇 为溶剂， 反应 3.5h， 生成 (3-甲氧苄基)甲基砜
  参考文献：
  名称：

  Discovery of a Potent and Selective Sphingosine Kinase 1 Inhibitor through the Molecular Combination of Chemotype-Distinct Screening Hits

  摘要：

  Sphingosine kinase (SphK) is the major source of the lipid mediator and G protein-coupled receptor agonist sphingosine-l-phosphate (S1P). SIP promotes cell growth, survival, and migration and is a key regulator of lymphocyte trafficking. Inhibition of SIP signaling has been proposed as a strategy for treatment of inflammatory diseases and cancer. Two different formats of an enzyme-based high-throughput screen yielded two attractive chemotypes capable of inhibiting SO formation in cells. The molecular combination of these screening hits led to compound 22a (PF-543) with 2 orders of magnitude improved potency. Compound 22a inhibited SphK1 with an IC50 of 2 nM and was more than 100-fold selective for SphK1 over the SphK2 isoform. Through the modification of tail-region substituents, the specificity of inhibition for SphK1 and SphK2 could be modulated, yielding SphK1-selective, potent SphK1/2 dual, or SphK2-preferential inhibitors.

  DOI：

  10.1021/acs.jmedchem.7b00070

文献信息

• Azetidine derivatives, their preparation and medicaments containing them
  申请人：——

  公开号：US20020035102A1

  公开（公告）日：2002-03-21

  The invention concerns compounds of formula (1) wherein: R represents a chain (A) or (B); R 1 is methyl or ethyl; R 2 is either an optionally substituted aromatic or an optionally substituted heteroaromatic ring; R 3 and R 4 , identical or different, are either an optionally substituted aromatic or an optionally substituted heteroaromatic ring; R′ represents a hydrogen atom or a —CO—alk radical, their optical isomers, their salts, their preparation and medicines containing them. 1

  本发明涉及通式(1)的化合物，其中：R代表链(A)或(B)；R1是甲基或乙基；R2是可任选取代的芳香环或可任选取代的杂芳香环；R3和R4，相同或不同，是可任选取代的芳香环或可任选取代的杂芳香环；R′代表氢原子或—CO—烷基，它们的光学异构体，它们的盐，它们的制备方法以及含有它们的药物。
• Heteroaryl substituted pyrrolo[2,3-b]pyridines and pyrrolo[2,3-b]pyrimidines as janus kinase inhibitors
  申请人：Rodgers D. James

  公开号：US20070135461A1

  公开（公告）日：2007-06-14

  The present invention provides heteroaryl substituted pyrrolo[2,3-b]pyridines and heteroaryl substituted pyrrolo[2,3-b]pyrimidines that modulate the activity of Janus kinases and are useful in the treatment of diseases related to activity of Janus kinases including, for example, immune-related diseases, skin disorders, myeloid proliferative disorders, cancer, and other diseases.

  本发明提供了杂环取代的吡咯并[2,3-b]吡啶和杂环取代的吡咯并[2,3-b]嘧啶，可以调节雅努斯激酶的活性，并且在治疗与雅努斯激酶活性相关的疾病中具有用处，例如免疫相关疾病、皮肤疾病、髓增生性疾病、癌症和其他疾病。
• Novel bicycloalkane derivatives and the production thereof
  申请人：Schering Aktiengesellschaft

  公开号：US04202991A1

  公开（公告）日：1980-05-13

  Bicycloalkane derivatives of the formula ##STR1## wherein n is 1 or 2, R.sub.1 is lower alkyl, Acyl is alkanoyl, and Y is --S--R.sub.2, --SO.sub.m --R.sub.2, or ##STR2## wherein m is 1 or 2, R.sub.2 is alkyl, R.sub.3 is hydrogen or lower alkyl, R.sub.4 is acyl or phenyl optionally substituted with lower alkoxy, benzyloxy or alkanoyloxy; and Z is nitro, lower alkoxycarbonyl, lower alkanoyl, lower alkylsulfinyl, or lower alkylsulfonyl are useful intermediates in the total synthesis of steroids. The compounds are prepared by reacting a corresponding compound lacking the CH.sub.2 Y substituent with formaldehyde and a mercaptan or sulfinic acid, followed if desired by oxidation and optional salt condensation.

  Bicycloalkane衍生物的化学式为##STR1##其中n为1或2，R.sub.1为低碳烷基，Acyl为烷酰基，Y为--S--R.sub.2，--SO.sub.m --R.sub.2或##STR2##其中m为1或2，R.sub.2为烷基，R.sub.3为氢或低碳烷基，R.sub.4为酰基或苯基，可选择地取代为低烷氧基、苄氧基或烷酰氧基；Z为硝基、低烷氧羰基、低烷酰基、低烷基亚砜基或低烷基砜基的化合物，在类固醇的全合成中是有用的中间体。这些化合物是通过将相应缺少CH.sub.2 Y取代基的化合物与甲醛和巯基或亚砜酸反应制备的，随后如有需要，进行氧化和可选的盐类缩合。
• Bicycloalkane derivatives
  申请人：Schering Aktiengesellschaft

  公开号：US04072716A1

  公开（公告）日：1978-02-07

  Bicycloalkane derivatives of the formula ##STR1## WHEREIN N IS 1 OR 2, R.sub.1 is lower alkyl, X is carbonyl or free or etherified hydroxymethylene, and Y is --S--R.sub.2, --SO.sub.m --R.sub.2, or ##STR2## wherein m is 1 or 2, R.sub.2 is alkyl, R.sub.3 is hydrogen or lower alkyl, R.sub.4 is aliphatic acyl and Z is nitro, lower alkanoyl, lower alkylsulfinyl, or lower alkylsulfonyl are useful intermediates in the total synthesis of steroids. The compounds are prepared by reacting a corresponding compound lacking the CH.sub.2 Y substituent with formaldehyde and a mercaptan or a sulfinic acid, followed if desired by oxidation and optional salt condensation.

  公式为##STR1##的双环烷衍生物，其中N为1或2，R.sub.1为较低的烷基，X为羰基或自由的或醚化的羟甲基，Y为--S--R.sub.2，--SO.sub.m --R.sub.2，或##STR2##其中m为1或2，R.sub.2为烷基，R.sub.3为氢或较低的烷基，R.sub.4为脂肪酰基，Z为硝基，较低的醇酰基，较低的烷基亚砜基，或较低的烷基磺酰基，在类固醇的全合成中是有用的中间体。这些化合物是通过将缺少CH.sub.2 Y取代基的相应化合物与甲醛和巯基或亚砜酸反应制备的，随后如有需要进行氧化和可选的盐缩合。
• HETEROARYL SUBSTITUTED PYRROLO[2,3-b]PYRIDINES AND PYRROLO[2,3-b]PYRIMIDINES AS JANUS KINASE INHIBITORS
  申请人：Rodgers James D.

  公开号：US20090181959A1

  公开（公告）日：2009-07-16

  The present invention provides heteroaryl substituted pyrrolo[2,3-b]pyridines and heteroaryl substituted pyrrolo[2,3-b]pyrimidines that modulate the activity of Janus kinases and are useful in the treatment of diseases related to activity of Janus kinases including, for example, immune-related diseases, skin disorders, myeloid proliferative disorders, cancer, and other diseases.

  本发明提供了杂环取代的吡咯并[2,3-b]吡啶和杂环取代的吡咯并[2,3-b]嘧啶，可调节Janus激酶的活性，并可用于治疗与Janus激酶活性相关的疾病，包括免疫相关疾病、皮肤疾病、髓系增生性疾病、癌症和其他疾病。