3-(N,N-dimethylamino)-1-(3,4,5-trimethoxyphenyl)propan-1-one | 39038-42-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(N,N-dimethylamino)-1-(3,4,5-trimethoxyphenyl)propan-1-one
• 英文别名: 3-(N,N-Dimethylamino)-1-(3,4,5-trimethoxyphenyl)-1-propanone；3-dimethylamino-1-(3,4,5-trimethoxy-phenyl)-propan-1-one；3-Dimethylamino-1-(3,4,5-trimethoxy-phenyl)-propan-1-on；3-(N,N-Dimethyl amino)-1-(3,4,5-trimethoxyphenyl)-1-propanone；3-dimethylamino-1-(3,4,5-trimethoxyphenyl)-1-propanone；3-(Dimethylamino)-1-(3,4,5-trimethoxyphenyl)propan-1-one
• CAS: 39038-42-1
• 化学式: C₁₄H₂₁NO₄
• mdl: MFCD10038747
• 分子量: 267.325
• InChiKey: ZHYLLQLGGCGWTQ-UHFFFAOYSA-N

物化性质

• 沸点：
  374.2±42.0 °C(Predicted)
• 密度：
  1.070±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(N,N-dimethylamino)-1-(3,4,5-trimethoxyphenyl)propan-1-one 在 sodium cyanide 、 sodium tetrahydroborate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.5h， 生成 1-phenyl-4-(3,4,5-trimethoxyphenyl)butane-1,4-diol
  参考文献：
  名称：

  Synthesis and trypanocidal activity of 1,4-bis-(3,4,5-trimethoxy-phenyl)-1,4-butanediol and 1,4-bis-(3,4-dimethoxyphenyl)-1,4-butanediol

  摘要：

  Chagas' disease is endemic in Central and South American countries. Specific chemotherapy with nifurtimox or benznidazole has been recommended for treatment of recent infection but they have limited efficacy. The natural products veraguensin (1) and grandisin (2) have shown potent in vitro activity against trypomastigote parasite (Y strain) with IC50 2.3 mu M (1) and 3.7 mu M (2). We report herein the synthesis and in vitro trypanocidal evaluation of symmetrical and unsymmetrical 1,4-diaryl-1,4-diol derivatives as potential trypanocidal analogs of natural compounds 1 and 2. Among the synthesized products, compounds 1,4-bis-(3,4,5-trimethoxyphenyl)-1,4-butanediol (6a) and 1,4-bis-(3,4-dimethoxyphenyl)-1,4-butanediol (6b) showed better activity against Trypanosoma cruzi trypomastigotes with IC50 100 and 105 mu M (Y strain), respectively, and 110 mu M (Bolivia strain) for both compounds. However, the most active compound of this series was 1,4-bis-(3,4-dimethoxyphenyl)butane-1,4-dione (7b) with IC50 10 and 200 mu M against Y and Bolivia strains, respectively. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.07.006
• 作为产物：
  描述：

  3',4',5'-三甲氧基苯乙酮 、 盐酸二甲胺 在 盐酸 、 paraformaldehyde 作用下， 以 乙醇 、 水 为溶剂， 以92%的产率得到3-(N,N-dimethylamino)-1-(3,4,5-trimethoxyphenyl)propan-1-one
  参考文献：
  名称：

  Compounds and methods for the treatment of cardiovascular, inflammatory

  摘要：

  揭示了能够减少中性粒细胞在炎症或免疫反应期间导致有害氧自由基形成的化合物，包括2,5-二芳基四氢呋喃、2,5-二芳基四氢噻吩、1,3-二芳基环戊烷。这些化合物通过作为PAF受体拮抗剂、抑制5-脂氧合酶酶或表现出双重活性（即既作为PAF受体拮抗剂又作为5-脂氧合酶抑制剂）来展示这种生物活性。还揭示了一种治疗由PAF和/或白三烯介导的疾病的方法，包括向需要此类治疗的患者投予上述化合物或其药学上可接受的盐中的一个或多个的有效量，可选地在药学上可接受的载体中。

  公开号：

  US05463083A1

文献信息

• Certain 2,5-diaryl tetrahydrofurans and analogs thereof as PAF
  申请人：Merck & Co. Inc.

  公开号：US05010100A1

  公开（公告）日：1991-04-23

  The present invention is directed to a specifically substituted tetrahydrofuran of the formula (I) ##STR1## wherein R.sup.4 is an alkylthio, alkylsulfinyl or alkylsulfonyl containing group, Y is an alkyl or substituted alkyl group and R.sup.6 is an alkoxy or a substituted alkoxy or alkyl group.

  本发明涉及具有以下结构的特定取代四氢呋喃化合物（I）##STR1##其中R.sup.4是含有烷基硫醚，烷基亚砜基或烷基砜基的基团，Y是烷基或取代烷基基团，R.sup.6是烷氧基或取代烷氧基或烷基基团。
• PHARMACEUTICAL FORMULATIONS USEFUL TO TREAT INFLAMMATORY AND IMMUNE DISORDERS
  申请人：——

  公开号：US20030008914A1

  公开（公告）日：2003-01-09

  A pharmaceutical formulation is provided for the treatment of inflammatory and/or immune disorders, particularly those mediated by platelet activating factor (“PAF”) or a product of 5-lipoxygenase. The formulation, in one embodiment, is an essentially anhydrous ointment containing an active agent selected from the group consisting of 2,5-diaryl tetrahydrofurans, 2,5-diaryl tetrahydrothiophenes, 2,4-diaryl tetrahydrofurans, 2,4-diaryl tetrahydrothiophenes, 1,3-diaryl cyclopentanes, 2,4-diaryl pyrrolidines, and 2,5-diaryl pyrrolidines, and an enhancer composition containing one or more C 3-18 esters such as diethyl succinate, propylene carbonate, diisopropyl adipate and glyceryl triacetate. In another embodiment, the formulation is a cream, gel, lotion, oil, or the like, containing the: active agent in crystalline form. The invention also encompasses the novel crystalline form of the active agent, and methods for using the formulations to treat individuals with inflammatory and/or immune disorders. Also encompassed is use of isopropyl alcohol (IPA) to enhance stability of the active agent and pharmaceutical formulations.

  提供了一种用于治疗炎症和/或免疫紊乱的制药配方，特别是那些由血小板活化因子（“PAF”）或5-脂氧合酶产物介导的疾病。在一个实施例中，该配方是一种基本无水的软膏，含有从2,5-二芳基四氢呋喃、2,5-二芳基四氢噻吩、2,4-二芳基四氢呋喃、2,4-二芳基四氢噻吩、1,3-二芳基环戊烷、2,4-二芳基吡咯烷和2,5-二芳基吡咯烷等化合物组成的活性剂，以及一个增效剂组合，其中包含一个或多个C3-18酯，如琥珀酸二乙酯、碳酸丙二酯、己二酸二异丙酯和三乙酰甘油。在另一个实施例中，该配方是一种乳霜、凝胶、乳液、油剂等，含有晶体形式的活性剂。该发明还涵盖了该活性剂的新晶体形式，以及使用这些配方治疗患有炎症和/或免疫紊乱的个体的方法。还包括异丙醇（IPA）用于增强活性剂和制药配方的稳定性。
• Compounds and methods for the treatment of cardiovascular, inflammatory and immune disorders
  申请人：Millennium Pharmaceuticals, Inc.

  公开号：US06420392B1

  公开（公告）日：2002-07-16

  2,5-Diaryl tetrahydrofurans, 2,5-diaryl tetrahydrothiophenes, 1,3-diaryl cyclopentanes are disclosed that reduce the chemotaxis and respiratory burst leading to the formation of damaging oxygen radicals of polymorphonuclear leukocytes during an inflammatory or immune response. The compounds exhibit this biological activity by acting as PAF receptor antagonists, by inhibiting the enzyme 5-lipoxygenase, or by exhibiting dual activity, i.e., by acting as both a PAF receptor antagonist and inhibitor of 5-lipoxygenase. Also disclosed is a method to treat disorders mediated by PAF and/or leukotrienes that includes administering an effective amount of one or more of the above-identified compounds or a pharmaceutically acceptable salt thereof, optionally in a pharmaceutically acceptable carrier, to a patient in need of such therapy.

  披露了可以减少多形核白细胞在炎症或免疫反应期间引起化学趋化和呼吸爆发，从而导致有害氧自由基形成的2,5-二芳基四氢呋喃、2,5-二芳基四氢噻吩、1,3-二芳基环戊烷。这些化合物通过作为PAF受体拮抗剂、抑制酶5-脂氧合酶，或表现出双重活性，即作为PAF受体拮抗剂和5-脂氧合酶抑制剂来展示这种生物活性。还公开了一种治疗由PAF和/或白三烯介导的疾病的方法，包括向需要此类治疗的患者投予上述识别的一个或多个化合物或其药学上可接受的盐的有效量，可选地在药学上可接受的载体中。
• Chromene-containing compounds with anti-tubulin and vascular targeting activity
  申请人：Pinney G. Kevin

  公开号：US20050245489A1

  公开（公告）日：2005-11-03

  Trimethoxyphenyl substituted indole ligands have been discovered which demonstrate impressive cytotoxicity as well as a remarkable ability to inhibit tubulin polymerization. Such compounds as well as related derivatives are excellent clinical candidates for the treatment of cancer in humans. In addition, certain of these ligands, as pro-drugs, may well prove to be tumor selective vascular targeting chemotherapeutic agents or to have vascular targeting activity resulting in the selective prevention and/or destruction of nonmalignant proliferating vasculature.

  已发现取代了三甲氧基苯基的吲哚配体，表现出令人印象深刻的细胞毒性以及抑制微管聚合的显著能力。这些化合物以及相关衍生物是治疗人类癌症的优秀临床候选药物。此外，这些配体中的某些作为前药，可能证明是肿瘤选择性血管靶向化疗药物，或具有血管靶向活性，从而选择性地预防和/或破坏非恶性增殖血管。
• Compounds and methods for the treatment of inflammatory and immune disorders
  申请人：——

  公开号：US20020177723A1

  公开（公告）日：2002-11-28

  2,5-Diaryl tetrahydrofurans, 2,5-diaryl tetrahydrothiophenes, 2,4-diaryl tetrahydrofurans, 2,4-diaryl tetrahydrothiophenes, 1,3-diaryl cyclopentanes, 2,4-diaryl pyrrolidines, and 2,5-diaryl pyrrolidines are disclosed that reduce the chemotaxis and respiratory burst leading to the formation of damaging oxygen radicals of polymorphonuclear leukocytes during an inflammatory or immune response. The compounds exhibit this biological activity by acting as PAF receptor antagonists, by inhibiting the enzyme 5-lipoxygenase, or by exhibiting dual activity, i. e., by acting as both a PAF receptor antagonist and inhibitor of 5-lipoxygenase. A method to treat disorders mediated by PAF or leukotrienes is also disclosed, that includes administering an effective amount of one or more of the above-identified compounds or a pharmaceutically acceptable salt thereof, optionally in a pharmaceutically acceptable carrier.

  本文披露了以下化合物：2,5-二芳基四氢呋喃，2,5-二芳基四氢噻吩，2,4-二芳基四氢呋喃，2,4-二芳基四氢噻吩，1,3-二芳基环戊烷，2,4-二芳基吡咯烷和2,5-二芳基吡咯烷，这些化合物可以减少多形核白细胞在炎症或免疫反应中的趋化和呼吸爆发，从而减少有害氧自由基的形成。这些化合物通过作为PAF受体拮抗剂、抑制5-脂氧合酶酶或表现出双重活性即同时作为PAF受体拮抗剂和5-脂氧合酶抑制剂来表现出这种生物活性。本文还披露了一种治疗PAF或白三烯介导的疾病的方法，包括在药学上可接受的载体中投与上述化合物或其药学上可接受的盐的有效量。