methyl 4-((methylsulfinyl)methyl)benzoate | 199534-98-0

• 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: methyl 4-((methylsulfinyl)methyl)benzoate
• 英文别名: Methyl 4-(methylsulfinylmethyl)benzoate
• CAS: 199534-98-0
• 化学式: C₁₀H₁₂O₃S
• 分子量: 212.269
• InChiKey: VSHMTIZCAHSHNT-UHFFFAOYSA-N

物化性质

• 沸点：
  411.4±38.0 °C(Predicted)
• 密度：
  1.251±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  62.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 4-((methylsulfinyl)methyl)benzoate 在 sodium hydroxide 作用下， 反应 1.0h， 以64%的产率得到4-Methanesulfinylmethyl-benzoic acid
  参考文献：
  名称：

  Design and Synthesis of Benzoic Acid Derivatives as Influenza Neuraminidase Inhibitors Using Structure-Based Drug Design

  摘要：

  A series of 94 benzoic acid derivatives was synthesized and tested for its ability to inhibit influenza neuraminidase. The enzyme-inhibitor complex structure was determined by X-ray crystallographic analysis for compounds which inhibited the enzyme. The most potent compound tested in vitro, 5 (4-(acetylamino)-3-guanidinobenzoic acid), had an IC50 = 2.5 x 10(-6) M against N9 neuraminidase. Compound 5 was oriented in the active site of the neuraminidase ina manner that was not predicted from the reported active site binding of GANA (4) with neuraminidase. In a mouse model of influenza, 5 did not protect the mice from weight loss due to the influenza virus when dosed intranasally.

  DOI：

  10.1021/jm970479e
• 作为产物：
  描述：

  4-溴甲基苯甲酸甲酯 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 methyl 4-((methylsulfinyl)methyl)benzoate
  参考文献：
  名称：

  Design and Synthesis of Benzoic Acid Derivatives as Influenza Neuraminidase Inhibitors Using Structure-Based Drug Design

  摘要：

  A series of 94 benzoic acid derivatives was synthesized and tested for its ability to inhibit influenza neuraminidase. The enzyme-inhibitor complex structure was determined by X-ray crystallographic analysis for compounds which inhibited the enzyme. The most potent compound tested in vitro, 5 (4-(acetylamino)-3-guanidinobenzoic acid), had an IC50 = 2.5 x 10(-6) M against N9 neuraminidase. Compound 5 was oriented in the active site of the neuraminidase ina manner that was not predicted from the reported active site binding of GANA (4) with neuraminidase. In a mouse model of influenza, 5 did not protect the mice from weight loss due to the influenza virus when dosed intranasally.

  DOI：

  10.1021/jm970479e

文献信息

• Methanesulfinylation of Benzyl Halides with Dimethyl Sulfoxide
  作者：Duo Fu、Jun Dong、Hongguang Du、Jiaxi Xu

  DOI：10.1021/acs.joc.9b03041

  日期：2020.2.21

  this transition-metal-free reaction, DMSO acts as not only a solvent but also a "S(O)Me" source, thus providing a convenient method for the efficient and direct synthesis of various benzyl methyl sulfoxides.

  已经开发了三溴化苯基三甲基铵介导的苄基卤化物与DMSO的亲核取代/氧转化反应。在该无过渡金属的反应中，DMSO不仅充当溶剂，而且充当“ S（O）Me”源，因此为有效且直接合成各种苄基甲基亚砜提供了一种便捷的方法。
• Selective Oxidation of Sulfides to Sulfoxides with Cetyltrimethylammonium Periodate
  作者：Umesh V. Chaudhari、Pradeep T. Deota

  DOI：10.1080/00304948.2012.697729

  日期：2012.1

  10 oxygen and t-BuOOH11 have been employed. Although, H2O2 is environmentally benign and NaIO4 may be stored and used safely, they oxidize sulfides slowly; for example, NaIO4 requires 12 hours or more,7,8 while H2O2 in the absence of catalyst requires 18 hours or more.12 Moreover H2O2 should be used in a controlled manner to avoid over-oxidation. Therefore most of the oxidizing agents are either hazardous

  硫化物选择性氧化为亚砜是一个重要的转变，1 因为亚砜是有用的构建块，尤其是作为手性助剂。2,3 此外，亚砜在获得许多具有生物学和化学意义的化合物方面也发挥着重要作用。 4-6 一些已使用过氧化氢 (H2O2)、高碘酸钠 (NaIO4)、m-CPBA、9 臭氧、10 氧气和 t-BuOOH11 等氧化剂。虽然 H2O2 对环境无害，NaIO4 可以安全储存和使用，但它们氧化硫化物的速度较慢；例如，NaIO4 需要 12 小时或更长时间，7,8 而 H2O2 在没有催化剂的情况下需要 18 小时或更长时间。12 此外，应以受控方式使用 H2O2 以避免过度氧化。因此，大多数氧化剂要么是危险的过氧酸，要么涉及有毒重金属或稀有氧化剂，难以制备，从而在许多情况下影响了它们的实际应用。以钒、钼、钨等金属的络合物或盐为催化剂的过氧化氢可选择性地提供亚砜。 1,13 多种氧化剂与作为催化剂的金属席夫碱络合物也已用于此目的；14，
• Synthesis and structure–activity relationship of potent, selective and orally active anthranilamide-based factor Xa inhibitors: Application of weakly basic sulfoximine group as novel S4 binding element
  作者：Vrajesh Pandya、Mukul Jain、Ganes Chakrabarti、Hitesh Soni、Bhavesh Parmar、Balaji Chaugule、Jigar Patel、Tushar Jarag、Jignesh Joshi、Nirav Joshi、Akshyaya Rath、Vishal Unadkat、Bhavesh Sharma、Haresh Ajani、Jeevan Kumar、Kalapatapu V.V.M. Sairam、Harilal Patel、Pankaj Patel

  DOI：10.1016/j.ejmech.2012.10.005

  日期：2012.12

  A novel series of potent and efficacious factor Xa inhibitors which possesses sulfoximine moiety as novel S4 binding element in anthranilamide chemotype has been identified. Lead optimization at this novel P4 group led to many potent factor Xa inhibitors with excellent anticoagulant activity in human plasma. Selected compounds were dosed orally in rats and checked for their ex vivo prothrombin time prolonging activity, which resulted in identification of compound 5-chloro-N-(5-chloropyridin-2-yl)-2-(4-(N-(2(diethylamino)acetyl)-S-methylsulfonimidoyl)benzamido)benzamide (18f). The detailed pharmacokinetic evaluation and subsequent metabolism study of 181 suggested the presence of an active metabolite. The compound 18f and its active metabolite 18b demonstrated excellent in vivo efficacy in both arterial and venous thrombosis model in rats and were found to be highly selective against related serine proteases. Based on this promising profile, compound 18f was selected for further evaluation. (C) 2012 Elsevier Masson SAS. All rights reserved.
• [EN] TGONOVEL HDAC INHIBITORS AND THERAPEUTIC USE THEREOF<br/>[FR] NOUVEAUX INHIBITEURS DE HDAC ET LEUR UTILISATION THÉRAPEUTIQUE
  申请人：[en]TANGO THERAPEUTICS, INC.

  公开号：WO2023102162A1

  公开（公告）日：2023-06-08

  Described herein are novel compounds, compositions and methods for treatment of diseases including cancer using such compounds, compositions, and methods. The compounds include those of Formula (I):
• Design and Synthesis of Benzoic Acid Derivatives as Influenza Neuraminidase Inhibitors Using Structure-Based Drug Design
  作者：Pooran Chand、Yarlagadda S. Babu、Shanta Bantia、Naiming Chu、L. Brent Cole、Pravin L. Kotian、W. Graeme Laver、John A. Montgomery、Ved P. Pathak、Sandra L. Petty、David P. Shrout、David A. Walsh、Gerald M. Walsh

  DOI：10.1021/jm970479e

  日期：1997.12.1

  A series of 94 benzoic acid derivatives was synthesized and tested for its ability to inhibit influenza neuraminidase. The enzyme-inhibitor complex structure was determined by X-ray crystallographic analysis for compounds which inhibited the enzyme. The most potent compound tested in vitro, 5 (4-(acetylamino)-3-guanidinobenzoic acid), had an IC50 = 2.5 x 10(-6) M against N9 neuraminidase. Compound 5 was oriented in the active site of the neuraminidase ina manner that was not predicted from the reported active site binding of GANA (4) with neuraminidase. In a mouse model of influenza, 5 did not protect the mice from weight loss due to the influenza virus when dosed intranasally.