phosphoric acid diethyl ester 4-[2-(4-isobutyl-phenyl)-propionylamino]-butyl ester | 1452560-18-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: phosphoric acid diethyl ester 4-[2-(4-isobutyl-phenyl)-propionylamino]-butyl ester
• 英文别名: Phosphoric acid diethyl ester 4-[2-(4-isobutyl-phenyl)-propionylamino]-butyl ester；diethyl 4-[2-[4-(2-methylpropyl)phenyl]propanoylamino]butyl phosphate
• CAS: 1452560-18-7
• 化学式: C₂₁H₃₆NO₅P
• 分子量: 413.494
• InChiKey: YQNUQUNJNKCCCJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  28
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  布洛芬 在 4-二甲氨基吡啶 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 phosphoric acid diethyl ester 4-[2-(4-isobutyl-phenyl)-propionylamino]-butyl ester
  参考文献：
  名称：

  PHOSPHO-ESTER DERIVATIVES AND USES THEREOF

  摘要：

  磷酸酯化合物及其制剂可通过呼吸道及其他途径用于预防和/或治疗肺癌和脑癌及其癌前病变条件，用于疼痛治疗，用于皮肤疾病治疗，用于治疗和/或预防与炎症相关的疾病，以及用于癌症的治疗和预防。

  公开号：

  US20130225529A1

文献信息

• COMPOUNDS AND COMPOSITIONS FOR USE IN THE TREATMENT AND PREVENTION OF LUNG AND BRAIN CANCER AND PRECANCEROUS CONDITIONS THEREOF
  申请人：Medicon Pharmaceuticals, Inc.

  公开号：US20140178461A1

  公开（公告）日：2014-06-26

  Novel compounds and pharmaceutical compositions thereof administered by the respiratory route for prevention and/or treatment of lung and brain cancer and precancerous conditions thereof.

  通过呼吸道给予的新化合物和其制药组合物，用于预防和/或治疗肺癌、脑癌及其癌前状态。
• Product Comprising a Nicotine-Containing Material and an Anti-Cancer Agent
  申请人：Rigas, Basil

  公开号：EP2711006A1

  公开（公告）日：2014-03-26

  The invention is directed to a product comprising a nicotine-containing material and an anti-cancer agent. The product is applicable in the treatment and/or prevention of cancer and precancerous conditions as well as for preventing cancer recurrence.

  本发明涉及一种由含尼古丁材料和抗癌剂组成的产品。该产品适用于治疗和/或预防癌症和癌前病变，以及预防癌症复发。
• A novel ibuprofen derivative with anti-lung cancer properties: Synthesis, formulation, pharmacokinetic and efficacy studies
  作者：Ka-Wing Cheng、Ting Nie、Nengtai Ouyang、Ninche Alston、Chi C. Wong、George Mattheolabakis、Ioannis Papayannis、Liqun Huang、Basil Rigas

  DOI：10.1016/j.ijpharm.2014.10.019

  日期：2014.12

  Phospho-non-steroidal anti-inflammatory drugs (phospho-NSAIDs) are a novel class of NSAID derivatives with potent antitumor activity. However, phospho-NSAIDs have limited stability in vivo due to their rapid hydrolysis by carboxylesterases at their carboxylic ester link. Here, we synthesized phospho-ibuprofen amide (PIA), a metabolically stable analog of phospho-ibuprofen, formulated it in nanocarriers, and evaluated its pharmacokinetics and anticancer efficacy in pre-clinical models of human lung cancer. PIA was 10-fold more potent than ibuprofen in suppressing the growth of human non-small-cell lung cancer (NSCLC) cell lines, an effect mediated by favorably altering cytokinetics and inducing oxidative stress. Pharmacokinetic studies in rats revealed that liposome-encapsulated PIA exhibited remarkable resistance to hydrolysis by carboxylesterases, remaining largely intact in the systemic circulation, and demonstrated selective distribution to the lungs. The antitumor activity of liposomal PIA was evaluated in a metastatic model of human NSCLC in mice. Liposomal PIA strongly inhibited lung tumorigenesis (>95%) and was significantly (p < 0.05) more efficacious than ibuprofen. We observed a significant induction of urinary 8-iso-prostaglandin F-2 alpha in vivo, which indicates that ROS stress probably plays an important role in mediating the antitumor efficacy of PIA. Our findings suggest that liposomal PIA is a potent agent in the treatment of lung cancer and merits further evaluation. (C) 2014 Elsevier B.V. All rights reserved.
• PRODUCT COMPRISING A NICOTINE-CONTAINING MATERIAL AND AN ANTI-CANCER AGENT
  申请人：Rigas Basil

  公开号：US20140088044A1

  公开（公告）日：2014-03-27

  The invention is directed to a product comprising a nicotine-containing material and an anti-cancer agent. The product is applicable in the treatment and/or prevention of cancer and precancerous conditions as well as for preventing cancer recurrence.
• COMPOUNDS AND COMPOSITIONS FOR USE IN THE PREVENTION AND TREATMENT OF INFLAMMATION-RELATED DISORDERS, PAIN AND FEVER, SKIN DISORDERS, CANCER AND PRECANCEROUS CONDITIONS THEREOF
  申请人：Medicon Pharmaceuticals, Inc.

  公开号：US20140315834A1

  公开（公告）日：2014-10-23

  The present invention provides novel compounds and pharmaceutical compositions for the prevention and/or treatment of cancer and precancerous conditions thereof, for the treatment of pain and fever, for the treatment of skin disorders, and for treating and/or preventing inflammation-related diseases and/or cardiovascular diseases. The compounds of the invention also have analgesic properties and anti-platelet properties. The compounds of the invention may be provided to animals, including mammals and humans, by administering a suitable pharmaceutical dose in a suitable pharmaceutical dosage form. The compounds of the invention have improved efficacy and safety, including higher potency and/or fewer or less severe side effects, than conventional therapies. The compounds of the invention comprise a biologically active moiety or portion (A) that has, or is modified to have at least one carboxyl group. The moiety A is preferably an aliphatic, aromatic or alkylaryl group, preferably derived from a non-steroidal anti-inflammatory drug or NSAID (A). The moiety A is bound to a linker moiety (B) via the carboxyl of group A and a linking atom that is selected from oxygen, nitrogen, and sulphur, to form a carboxylic ester, and amide, or a thioester, bond (X 1 ) between groups A and B. Moiety B is a single bond, an aliphatic group, a substituted benzene, or an alkylene substituted hydrocarbon chain, which in turn is bound to functional moiety Z, which facilitates access of the compound into cells. The moiety Z can comprise, for example, a phosphorous-containing group, a nitrogen-containing group, or a folic acid residue.