4-(2,3-dihydroxypropoxy)benzaldehyde | 64049-49-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-(2,3-dihydroxypropoxy)benzaldehyde
• 英文别名: rac-4-(2,3-dihydroxy-propoxy)-benzaldehyde
• CAS: 64049-49-6
• 化学式: C₁₀H₁₂O₄
• 分子量: 196.203
• InChiKey: QEZPUQMNWKYVDS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2912499000

反应信息

• 作为反应物：
  描述：

  4-(2,3-dihydroxypropoxy)benzaldehyde 在 sodium azide 、 对甲苯磺酸 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.5h， 生成 1-(2,3-diazidopropoxy)-4-(dimethoxymethyl)benzene
  参考文献：
  名称：

  pH可裂解的dPG-胺的合成，用于基因传递。

  摘要：

  由于许多现有的聚阳离子纳米载体的高毒性，用于基因治疗的有效非病毒载体的开发仍然是研究中的挑战。在本文中，描述了两种基于pH值可裂解的聚甘油胺基纳米载体的开发。苯乙缩醛键代表树突状聚甘油（dPG）与可复杂遗传物质的甘油基1,2-二胺之间的pH敏感切割位点。由于乙缩醛部分的酸不稳定性，可裂解的dPG-胺在体外毒性较小。细胞介导的降解会导致无毒的dPG，具有低胺官能度和低分子量裂解产物（cp）。由于多价胺基的丢失，遗传物质被释放。有趣的是，内体pH值下的释放动力学可以通过对乙缩醛进行简单的化学修饰来控制。体外实验表明，可裂解的dPG-胺具有用GFP-DNA转染HeLa细胞的能力，从而产生了与细胞相容的裂解产物。

  DOI：

  10.1002/mabi.201600190
• 作为产物：
  描述：

  比索洛尔杂质4 在 sodium hydroxide 作用下， 反应 3.0h， 以57%的产率得到4-(2,3-dihydroxypropoxy)benzaldehyde
  参考文献：
  名称：

  Synthesis and biological evaluation of novel 4-hydroxybenzaldehyde derivatives as tyrosinase inhibitors

  摘要：

  A series of novel 4-hydroxybenzaldehyde derivatives were synthesized and their inhibitory effects on the diphenolase activity of mushroom tyrosinase were investigated. Most of target compounds had more potent inhibitory activities than the parent compound 4-hydroxybenzaldehyde (IC50 = 1.22 mM). Interestingly, compound 3c bearing a dimethoxyl phosphate was found to be the most potent inhibitor with IC50 value of 0.059 mM. The inhibition kinetics analyzed by Lineweaver-Burk plots revealed that compound 3c was a non-competitive inhibitor (K-I = 0.0368 mM). In particular, compound 3c showed no side effects at dose of 1600 mg/kg in mice. These results suggested that such compounds might be served as lead compounds for further designing new potential tyrosinase inhibitors. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.11.007

文献信息

• 2-Imino-thiazolidin-4-one Derivatives as Potent, Orally Active S1P₁Receptor Agonists
  作者：Martin H. Bolli、Stefan Abele、Christoph Binkert、Roberto Bravo、Stephan Buchmann、Daniel Bur、John Gatfield、Patrick Hess、Christopher Kohl、Céline Mangold、Boris Mathys、Katalin Menyhart、Claus Müller、Oliver Nayler、Michael Scherz、Gunther Schmidt、Virginie Sippel、Beat Steiner、Daniel Strasser、Alexander Treiber、Thomas Weller

  DOI：10.1021/jm100181s

  日期：2010.5.27

  through five specific G-protein coupled receptors numbered S1P1 through S1P5. Agonists of the S1P1 receptor block the egress of T-lymphocytes from thymus and lymphoid organs and hold promise for the oral treatment of autoimmune disorders. Here, we report on the discovery and detailed structure−activity relationships of a novel class of S1P1 receptor agonists based on the 2-imino-thiazolidin-4-one scaffold

  鞘氨醇-1-磷酸酯（S1P）是一种广泛的溶血磷脂，具有丰富的生物学效应。细胞外S1P通过五个特定的G蛋白偶联受体S1P 1至S1P 5传递其活性。S1P 1受体激动剂阻止T淋巴细胞从胸腺和淋巴器官流出，并有望用于自身免疫性疾病的口服治疗。在这里，我们报告的发现和详细的结构与活性之间的关系基于2-亚氨基-噻唑烷酮-4-酮骨架的新型S1P 1受体激动剂。化合物8bo（ACT- 128800）从该系列中出现，是一种有效的，选择性的，口服活性的S1P 1选择受体激动剂进行临床开发。在大鼠中，以3 mg / kg的剂量达到最大程度的循环淋巴细胞减少。淋巴细胞隔离的持续时间是剂量依赖性的。在100 mg / kg的剂量下，对淋巴细胞计数的影响在不到36小时内是完全可逆的。8bo在比格犬中的药代动力学研究表明，该化合物适合于人类每天一次给药。
• Amberlite-IR 120 catalyzed three-component synthesis of α-amino phosphonates in one-pot
  作者：Asish K. Bhattacharya、Kalpeshkumar C. Rana

  DOI：10.1016/j.tetlet.2008.02.102

  日期：2008.4

  A simple, efficient, and environmentally benign method for a three-component reaction of an amine, an aldehyde or a ketone, and diethyl phosphite catalyzed by Amberlite-IR 120 resin has been developed to afford α-amino phosphonates in high yields and short reaction times under solvent-free reaction conditions. The major advantages of the present method are good yields, inexpensive, ecofriendly and

  已开发出一种简单，有效且环境友好的方法，用于由Amberlite-IR 120树脂催化的胺，醛或酮与亚磷酸二乙酯的三组分反应，从而以高收率和短反应时间提供α-氨基膦酸酯无溶剂反应条件下的反应时间。本方法的主要优点是产率高，价格便宜，生态友好且可重复使用的催化剂，温和且无溶剂的反应条件以及对基质中存在的各种功能的耐受性。
• [EN] 5-(BENZ- (Z) -YLIDENE) -THIAZOLIDIN-4-ONE DERIVATIVES AS IMMUNOSUPPRESSANT AGENTS<br/>[FR] DERIVES DE 5-(BENZ-(Z)-YLIDENE)-THIAZOLIDINE-4-ONE UTILISES COMME AGENT IMMUNODEPRESSEURS
  申请人：ACTELION PHARMACEUTICALS LTD

  公开号：WO2005054215A1

  公开（公告）日：2005-06-16

  The invention relates to pharmaceutical compositions containing at least one 5- (benz- (Z) -ylidene-thiazolidin-4-one derivative (I), to prevent or treat disorders associated with an activated immune system. Furthermore, the invention relates to novel thiazolidin-4-one derivatives notably for use as pharmaceutically active compounds. Said compounds particularly act also as immunosuppressive agents.

  这项发明涉及含有至少一种5-(苯基(Z)-基噻唑烷酮衍生物(I)的药物组合物，用于预防或治疗与激活的免疫系统相关的疾病。此外，该发明涉及新型噻唑烷酮衍生物，特别用作药用活性化合物。这些化合物特别还作为免疫抑制剂起作用。
• An Efficient One-Pot Synthesis of α-Amino Phosphonates Catalyzed by Bismuth Nitrate Pentahydrate
  作者：Asish Bhattacharya、Tanpreet Kaur

  DOI：10.1055/s-2007-970762

  日期：2007.3

  A simple, efficient, and environmentally benign method has been developed for the synthesis of α-amino phosphonates through a one-pot reaction of aldehydes with amines and diethyl phosphite in the presence of bismuth nitrate pentahydrate as a catalyst. Some of the major advantages of this protocol are: good yields, the involvement of a less-expensive and non-toxic catalyst, mild and solvent-free reaction conditions and also tolerance towards other functional groups present in the substrates. Eighteen examples are described, highlighting the substrate scope of the reaction.

  在五水硝酸铋作为催化剂的存在下，通过醛与胺和亚磷酸二乙酯的一锅反应合成δ-氨基膦酸盐，开发出了一种简单、高效且对环境无害的方法。该方法的一些主要优点包括：产率高、使用的催化剂成本较低且无毒、反应条件温和且无溶剂、对底物中存在的其他官能团具有耐受性。本文介绍了 18 个实例，突出了该反应的底物范围。
• Novel thiazolidin-4-one derivatives
  申请人：Binkert Christoph

  公开号：US20070082933A1

  公开（公告）日：2007-04-12

  The invention relates to pharmaceutical compositions containing at least one thiazolidin-4-one derivative to prevent or treat disorders associated with an activated immune system. Furthermore, the invention relates to novel thiazolidin-4-one derivatives notably for use as pharmaceutically active compounds. Said compounds particularly act also as immunosuppressive agents.

  本发明涉及包含至少一种噻唑烷-4-酮衍生物的药物组合物，用于预防或治疗与激活的免疫系统相关的疾病。此外，本发明涉及新型噻唑烷-4-酮衍生物，特别用作药物活性化合物。这些化合物还特别作为免疫抑制剂发挥作用。