2-ethoxy-6-pentadecylbenzoyl chloride | 485386-83-2

• 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: 2-ethoxy-6-pentadecylbenzoyl chloride
• 英文别名: 2-ethoxy-6-pentadecylbenzoic acid chloride；2-ethoxy-6-pentadecyl-benzoyl Chloride
• CAS: 485386-83-2
• 化学式: C₂₄H₃₉ClO₂
• 分子量: 395.025
• InChiKey: LWSRBDDNXXYSBA-UHFFFAOYSA-N

物化性质

• 沸点：
  491.4±33.0 °C(Predicted)
• 密度：
  0.978±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.6
• 重原子数：
  27
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-ethoxy-6-pentadecylbenzoyl chloride 在 氯磺酸 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 水 、 xylene 为溶剂， 反应 44.0h， 生成 5-[2-ethoxy-5-(4-methylpiperazin-1-ylsulfonyl)-6-pentadecylphenyl]-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one
  参考文献：
  名称：

  Synthesis of Sildenafil Analogues from Anacardic Acid and Their Phosphodiesterase-5 Inhibition

  摘要：

  Anacardic acid (6-pentadecylsalicylic acid), a major component of cashew nut shell liquid, consists of a heterogeneous mixture of monoenes, dienes, and trienes. The enes mixture of anacardic acid was hydrogenated to a saturated compound. Using saturated anacardic acid as a starting material, analogues of sildenafil [a potent phosphodiesterase-5 (PDE5) inhibitor and an orally active drug for the treatment of erectile dysfunction] were synthesized, to observe the effect of the pentadecyl side chain on PDE5 inhibition. The synthesized compounds were characterized by spectral studies and tested for PDE5 inhibition, and the results were compared With those obtained with sildenafil.

  DOI：

  10.1021/jf0258050
• 作为产物：
  描述：

  ethyl 2-ethoxy-6-pentadecylbenzoate 在 氯化亚砜 、 potassium tert-butylate 、 N,N-二甲基甲酰胺 作用下， 以 正己烷 、 二甲基亚砜 为溶剂， 反应 3.0h， 生成 2-ethoxy-6-pentadecylbenzoyl chloride
  参考文献：
  名称：

  Synthesis of Sildenafil Analogues from Anacardic Acid and Their Phosphodiesterase-5 Inhibition

  摘要：

  Anacardic acid (6-pentadecylsalicylic acid), a major component of cashew nut shell liquid, consists of a heterogeneous mixture of monoenes, dienes, and trienes. The enes mixture of anacardic acid was hydrogenated to a saturated compound. Using saturated anacardic acid as a starting material, analogues of sildenafil [a potent phosphodiesterase-5 (PDE5) inhibitor and an orally active drug for the treatment of erectile dysfunction] were synthesized, to observe the effect of the pentadecyl side chain on PDE5 inhibition. The synthesized compounds were characterized by spectral studies and tested for PDE5 inhibition, and the results were compared With those obtained with sildenafil.

  DOI：

  10.1021/jf0258050

文献信息

• Modulators (inhibitors/ activators) of histone acetyltransferases
  申请人：Kundu Kumar Tapas

  公开号：US20060167107A1

  公开（公告）日：2006-07-27

  Disclosed are compounds of the formulae: and method of using the compounds to treat cancer, AIDS, HIV infection, and asthma.

  揭示了以下式的化合物： 以及使用这些化合物治疗癌症、艾滋病、HIV感染和哮喘的方法。
• Synthesis of benzamide derivatives of anacardic acid and their cytotoxic activity
  作者：Venkateshappa Chandregowda、Anil Kush、Goukanapalli Chandrasekara Reddy

  DOI：10.1016/j.ejmech.2009.01.033

  日期：2009.6

  Several benzamide derivatives were synthesized from anacardic acid (1a) which was the product of hydrogenation of the naturally occurring anacardic acid mixture (1a–d), a major constituent of cashew nut shell liquid. Anacardic acid (1a) was first alkylated followed by hydrolysis of the ester to obtain synthones namely, 2-ethoxy-6-pentadecylbenzoic acid (5) and 2-isopropoxy-6-pentadecylbenzoic acid

  从腰果酸（1a）合成了几种苯甲酰胺衍生物，其是腰果壳液的主要成分，天然的腰果酸混合物（1a - d）的氢化产物。首先使去甲酸（1a）烷基化，然后将酯水解以获得合成酮，即2-乙氧基-6-十五烷基苯甲酸（5）和2-异丙氧基-6-十五烷基苯甲酸（6）。然后将这些水杨酸衍生物与各种苯胺偶联，以获得新颖的苯甲酰胺化合物（7 – 39）。测试了这些合成化合物对野生型HeLa细胞系（具有相对较高的p300表达）和HCT-15（p300阴性）的细胞毒作用。在所有化合物中，2-异丙氧基-6-十五烷基-N-吡啶-4-基苯甲酰胺（27），2-乙氧基-N-（3-硝基苯基）-6-十五烷基苯甲酰胺（22）和2-乙氧基-6-十五烷基发现-N-吡啶-4-基苯甲酰胺（10）在HeLa细胞系中的IC 50值分别为11.02μM，13.55μM，15.29μM时更有效。它们的活性与藤黄醇相当，后者是一种细胞可渗透的组蛋白乙酰转
• MODULATORS (INHIBITORS/ACTIVATORS) OF HISTONE ACETYLTRANSFERASES
  申请人：Kundu Tapas Kumar

  公开号：US20090076155A1

  公开（公告）日：2009-03-19

  The invention provides the use of certain benzoic acid and benzamide compounds as modulators of enzymes histone acetyltransferases, which are involved in gene expression and cancer and also use of such compounds in the treatment of diseases due to defects in gene regulation predominantly cancer.

  本发明提供了某些苯甲酸和苯甲酰胺化合物作为组蛋白乙酰转移酶酶调节剂的用途，该酶参与基因表达和癌症，并且还使用这些化合物治疗由基因调节缺陷引起的疾病，主要是癌症。
• Modulators (inhibitors/activators) of histone acetyltransferases
  申请人：Jawaharlal Nehru Centre for Advanced Scientific Research

  公开号：US07332629B2

  公开（公告）日：2008-02-19

  Disclosed are compounds of the formulae: and method of using the compounds to treat cancer, AIDS, HIV infection, and asthma.

  本发明涉及以下公式的化合物以及使用这些化合物治疗癌症、艾滋病、HIV感染和哮喘的方法。
• US7332629B2
  申请人：——

  公开号：US7332629B2

  公开（公告）日：2008-02-19