sulindac sulfide methyl ester | 106647-49-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚和异茚
• 英文名称: sulindac sulfide methyl ester
• 英文别名: methyl (Z)-2-(5-fluoro-2-methyl-1-(4-(methylthio)benzylidene)-1H-inden-3-yl)acetate；methyl (Z)-5-fluoro-2-methyl-1-(4-methylthiobenzylidene)inden-3-ylacetate；methyl 2-[(3Z)-6-fluoro-2-methyl-3-[(4-methylsulfanylphenyl)methylidene]inden-1-yl]acetate
• CAS: 106647-49-8
• 化学式: C₂₁H₁₉FO₂S
• 分子量: 354.445
• InChiKey: MYVOADOTMNPIRT-ZDLGFXPLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  sulindac sulfide methyl ester 在 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 、 potassium hydroxide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醇 、 水 、 乙腈 为溶剂， 反应 15.17h， 生成 (Z)-N-(2-(diethylamino)ethyl)-N-ethyl-2-(5-fluoro-2-methyl-1-(4-(methylthio)benzylidene)-1H-inden-3-yl)propanamide
  参考文献：
  名称：

  A small diversity library of α-methyl amide analogs of sulindac for probing anticancer structure-activity relationships

  摘要：

  Non-steroidal anti-inflammatory drugs (NSAIDs) have a variety of potential indications that include management of pain and inflammation as well as chemoprevention and/or treatment of cancer. Furthermore, a specific form of ibuprofen, dexibuprofen or the S-(+) form, shows interesting neurological activities and has been proposed for the treatment of Alzheimer's disease. In a continuation of our work probing the anticancer activity of small sulindac libraries, we have prepared and screened a small diversity library of alpha-methyl substituted sulindac amides in the profen class. Several compounds of this series displayed promising activity compared with a lead sulindac analog.

  DOI：

  10.1016/j.bmcl.2018.05.023
• 作为产物：
  描述：

  硫化舒林酸 在 氯化亚砜 作用下， 以 甲醇 为溶剂， 生成 sulindac sulfide methyl ester
  参考文献：
  名称：

  Indenyl hydroxamic acids, (hydroxy) ureas and urethanes for treating

  摘要：

  吲哚羟羧酸，(羟基)脲和脲醚在治疗癌前病变和肿瘤中很有用。

  公开号：

  US06071934A1

文献信息

• Indenyl hydroxamic acids and hydroxy ureas as inhibitors of
  申请人：Merck Frosst Canada, Inc.

  公开号：US05093356A1

  公开（公告）日：1992-03-03

  Compounds having the formula I: ##STR1## are inhibitors of the 5-lipoxygenase enzyme. These compounds are useful as anti-asthmatic, anti-allergic, anti-inflammatory, and cytoprotective agents. They are also useful in treating diarrhea, hypertension, angina, platelet aggregation, cerebral spasm, premature labor, spontaneous abortion, dysmenorrhea, and migraine.

  具有以下化学式的化合物：##STR1## 是5-脂氧合酶酶的抑制剂。这些化合物可用作抗哮喘、抗过敏、抗炎和细胞保护剂。它们还可用于治疗腹泻、高血压、心绞痛、血小板聚集、脑痉挛、早产、自发流产、痛经和偏头痛。
• Asymmetric synthesis of Sulindac esters by enantioselective sulfoxidation in the presence of chiral titanium complexes
  作者：Francesco Naso、Cosimo Cardellicchio、Francesco Affortunato、Maria Annunziata M. Capozzi

  DOI：10.1016/j.tetasy.2006.12.002

  日期：2006.12

  anti-cancer therapy. The key step of the overall procedure was the enantioselective hydroperoxide oxidation of the Sulindac sulfide alkyl esters in the presence of chiral complexes of titanium with either (S,S)- or (R,R)-hydrobenzoin. Various reaction conditions were investigated in order to obtain the best balance between yield and enantioselectivity.

  在制备舒林酸烷基酯时，获得了较高的ee值（高达94–96％ee）和中等的孤立产率（48–50％）。这些分子是舒林酸的简单直接的前体，舒林酸是一种抗炎药，最近也已在抗癌疗法中进行了研究。整个过程的关键步骤是在钛与（S，S）-或（R，R）-氢安息香的手性络合物存在下，对舒林酸硫化物烷基酯的对映选择性氢过氧化物氧化。为了获得收率和对映选择性之间的最佳平衡，研究了各种反应条件。
• Indenyl hydroxamic acids, (hydroxy) ureas and urethanes for treating patients with precancerous lesions
  申请人：Cell Pathways, Inc.

  公开号：US06300346B1

  公开（公告）日：2001-10-09

  Indenyl hydroxamic acids, (hydroxy) ureas and urethanes are useful in the treatment of precancerous lesions and neoplasms.

  Indenyl羟肟酸，（羟基）脲和脲醇在预防癌前病变和肿瘤治疗中很有用。
• Triethyl amine as an effective reducing agent for sulfoxide deoxygenation
  作者：Xiaojing Gao、Fumin Chen、Ming Yu Jin、Chen Xu

  DOI：10.1039/d4ob00219a

  日期：——

  Enabled by triethyl amine (Et3N) and thionyl chloride (SOCl2), an efficient and practical protocol for deoxygenation of sulfoxide to sulfide was developed. This new method features a wide range of substrate scope, including diaryl, dialkyl and aryl alkyl substituted sulfoxides. Detailed mechanistic investigations reveal the crucial role played by Et3N as an electron-donating reductant rather than a

  在三乙胺 (Et 3 N) 和亚硫酰氯 (SOCl 2 ) 的支持下，开发了一种有效且实用的亚砜脱氧为硫化物的方案。这种新方法的特点是底物范围广泛，包括二芳基、二烷基和芳烷基取代的亚砜。详细的机理研究揭示了 Et 3 N 作为电子供给还原剂而不是氢原子供体所发挥的关键作用。
• Indenyl hydroxamic acids, (hydroxy) ureas and urethanes for treating
  申请人：Cell Pathways, Inc.

  公开号：US06071934A1

  公开（公告）日：2000-06-06

  Indenyl hydroxamic acids, (hydroxy) ureas and urethanes are useful in the treatment of precancerous lesions and neoplasms.

  吲哚羟羧酸，(羟基)脲和脲醚在治疗癌前病变和肿瘤中很有用。