3-氯-4-乙氧基苯甲醛 | 99585-10-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 3-氯-4-乙氧基苯甲醛
• 英文名称: 3-chloro-4-ethoxybenzaldehyde
• 英文别名: 4-ethoxy-3-chloro-benzaldehyde；4-Aethoxy-3-chlor-benzaldehyd
• CAS: 99585-10-1
• 化学式: C₉H₉ClO₂
• mdl: MFCD06246171
• 分子量: 184.622
• InChiKey: ZYDPBMFCTQAEMR-UHFFFAOYSA-N

物化性质

• 沸点：
  283.8±20.0 °C(Predicted)
• 密度：
  1.202±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2913000090
• 危险性防范说明：
  P264,P280,P302+P352,P305+P351+P338,P332+P313,P337+P313,P362
• 危险性描述：
  H315,H319

反应信息

• 作为反应物：
  描述：

  3-氯-4-乙氧基苯甲醛 在 盐酸 、 甲酸 、 四氢可的松 、 三乙胺 作用下， 反应 16.0h， 生成 1-chloro-4-(3-chloro-4-ethoxybenzyl)amino-6-cyano-phthalazine
  参考文献：
  名称：

  4-Benzylamino-1-chloro-6-substituted Phthalazines:  Synthesis and Inhibitory Activity toward Phosphodiesterase 5

  摘要：

  We synthesized various 4-benzylamino-1-chloro-6-substituted phthalazines (15) and 4-benzylamino-1-chloro-7-substituted phthalazines (16) and evaluated their inhibitory activity toward phosphodiesterase 5 (PDE5) purified from porcine platelets. The PDE5-inhibitory activities of 15 were greater than those of the isomers (16). The preferred substituent at the 4-position of phthalazine was a (3-chloro-4-methoxybenzyl)amino group, and those at the B-position were cyano, nitro, and trifluoromethyl groups. Compounds 15a (IC50 = 4.8 nM), 15f (3.5 nM), and 15i (5.3 nM) were more potent inhibitors than E4021 (8.6 nM). Compounds 15a and 15f also showed vasorelaxant activity in isolated porcine coronary arteries precontracted with prostaglandin F-2 alpha (10(-5) M). The EC50 values for vasorelaxant action of 15a, 15f, and E4021 were 150, 160, and 980 nM, respectively. These results show that novel PDE5 inhibitors possessing a potent vasorelaxant effect may exist among phthalazine derivatives.

  DOI：

  10.1021/jm970815r
• 作为产物：
  描述：

  4-乙氧基苯甲醛 在 吡啶 、 磺酰氯 作用下， 生成 3-氯-4-乙氧基苯甲醛
  参考文献：
  名称：

  4-Benzylamino-1-chloro-6-substituted Phthalazines:  Synthesis and Inhibitory Activity toward Phosphodiesterase 5

  摘要：

  We synthesized various 4-benzylamino-1-chloro-6-substituted phthalazines (15) and 4-benzylamino-1-chloro-7-substituted phthalazines (16) and evaluated their inhibitory activity toward phosphodiesterase 5 (PDE5) purified from porcine platelets. The PDE5-inhibitory activities of 15 were greater than those of the isomers (16). The preferred substituent at the 4-position of phthalazine was a (3-chloro-4-methoxybenzyl)amino group, and those at the B-position were cyano, nitro, and trifluoromethyl groups. Compounds 15a (IC50 = 4.8 nM), 15f (3.5 nM), and 15i (5.3 nM) were more potent inhibitors than E4021 (8.6 nM). Compounds 15a and 15f also showed vasorelaxant activity in isolated porcine coronary arteries precontracted with prostaglandin F-2 alpha (10(-5) M). The EC50 values for vasorelaxant action of 15a, 15f, and E4021 were 150, 160, and 980 nM, respectively. These results show that novel PDE5 inhibitors possessing a potent vasorelaxant effect may exist among phthalazine derivatives.

  DOI：

  10.1021/jm970815r

文献信息

• Synthesis and Structure−Activity Relationship of a New Series of COX-2 Selective Inhibitors:  1,5-Diarylimidazoles
  作者：Carmen Almansa、José Alfón、Alberto F. de Arriba、Fernando L. Cavalcanti、Ignasi Escamilla、Luis A. Gómez、Agustí Miralles、Robert Soliva、Javier Bartrolí、Elena Carceller、Manuel Merlos、Julián García-Rafanell

  DOI：10.1021/jm030765s

  日期：2003.7.1

  The synthesis and the pharmacological activity of a series of 1,5-diarylimidazoles developed as potent and selective cyclooxygenase-2 (COX-2) inhibitors are described. The new compounds were evaluated both in vitro (COX-1 and COX-2 inhibition in human whole blood) and in vivo (carrageenan-induced paw edema, air-pouch, and hyperalgesia tests). Modification of all the positions of two regioisomeric imidazole

  描述了开发为有效和选择性环氧合酶2（COX-2）抑制剂的一系列1,5-二芳基咪唑的合成和药理活性。在体外（在人全血中对COX-1和COX-2的抑制）和在体内（对角叉菜胶引起的爪水肿，气袋和痛觉过敏测试）均对新化合物进行了评估。修饰两个区域异构咪唑核的所有位置导致鉴定出最佳的4- [4-氯-5-（3-氟-4-甲氧基苯基）咪唑-1-基]苯磺酰胺（UR-8880，51f）候选者，目前正在进行I期临床试验。
• Novel imidazole derivatives with anti-inflammatory activity
  申请人：——

  公开号：US20030176481A1

  公开（公告）日：2003-09-18

  Novel imidazole derivatives of formula I and their salts, solvates and prodrugs, wherein the meanings of the different radicals are as shown in the description. Said compounds are useful as anti-inflammatory agents. 1

  新型咪唑衍生物的化学式I及其盐类、溶剂合物和前药，其中不同基团的含义如描述中所示。这些化合物可用作抗炎药物。
• [EN] S1P RECEPTORS MODULATORS<br/>[FR] MODULATEURS DES RÉCEPTEURS S1P
  申请人：AKAAL PHARMA PTY LTD

  公开号：WO2010042998A1

  公开（公告）日：2010-04-22

  The invention relates to novel compounds that have S1P receptor modulating activity and, preferably, apoptotic activity and/or anti proliferative activity against cancer cells and other cell types. Further, the invention relates to a pharmaceutical comprising at least one compound of the invention for the treatment of diseases and/or conditions caused by or associated with inappropriate S1P receptor modulating activity or expression, for example, cancer. A further aspect of the invention relates to the use of a pharmaceutical comprising at least one compound of the invention for the manufacture of a medicament for the treatment of diseases and/or conditions caused by or associated with inappropriate S1P receptor modulating activity or expression such as cancer.

  该发明涉及具有S1P受体调节活性的新化合物，最好具有对癌细胞和其他细胞类型具有凋亡活性和/或抗增殖活性。此外，该发明涉及包含该发明中至少一种化合物的药物，用于治疗由不当的S1P受体调节活性或表达引起或相关的疾病和/或病况，例如癌症。该发明的另一个方面涉及使用包含该发明中至少一种化合物的药物制备药物，用于治疗由不当的S1P受体调节活性或表达引起或相关的疾病和/或病况，如癌症。
• Discovery of Novel Sphingosine-1-Phosphate-1 Receptor Agonists for the Treatment of Multiple Sclerosis
  作者：Sun Jun Park、Seul Ki Yeon、Yoowon Kim、Hyeon Jeong Kim、Siwon Kim、Jushin Kim、Ji Won Choi、Byungeun Kim、Elijah Hwejin Lee、Rium Kim、Seon Hee Seo、Jaeick Lee、Jun Woo Kim、Ha-Yeon Lee、Hayoung Hwang、Yong-Sun Bahn、Eunji Cheong、Jong-Hyun Park、Ki Duk Park

  DOI：10.1021/acs.jmedchem.1c01979

  日期：2022.2.24

  The sphingosine-1-phosphate-1 (S1P1) receptor agonists have great potential for the treatment of multiple sclerosis (MS) because they can inhibit lymphocyte egress through receptor internalization. We designed and synthesized triazole and isoxazoline derivatives to discover a novel S1P1 agonist for MS treatment. Of the two scaffolds, the isoxazoline derivative was determined to have excellent in vitro

  1-磷酸鞘氨醇 (S1P 1 ) 受体激动剂具有治疗多发性硬化症 (MS) 的巨大潜力，因为它们可以通过受体内化抑制淋巴细胞的排出。我们设计并合成了三唑和异恶唑啉衍生物，以发现一种用于 MS 治疗的新型 S1P 1激动剂。在这两种支架中，异恶唑啉衍生物被确定具有优异的体外疗效和药物样特性。其中，化合物21l被发现具有优异的药物样特性以及出色的体外功效（β-抑制蛋白募集中的EC 50 = 7.03 nM 和内化中的 EC 50 = 11.8 nM）。我们也确认了在实验性自身免疫性脑炎 MS 小鼠模型中， 21l有效抑制外周淋巴细胞计数试验中的淋巴细胞流出，显着提高了临床评分。
• [EN] INHIBITORS OF ACETYL-COA CARBOXYLASE<br/>[FR] INHIBITEURS DE L'ACÉTYL-COA CARBOXYLASE
  申请人：FOREST LAB HOLDINGS LTD

  公开号：WO2010127212A1

  公开（公告）日：2010-11-04

  The present invention relates to compounds that act as acetyl-CoA carboxylase (ACC) inhibitors. The invention also relates to methods of preparing the compounds, compositions containing the compounds, and to methods of treatment using the compounds.

  本发明涉及作为乙酰辅酶A羧化酶（ACC）抑制剂的化合物。该发明还涉及制备这些化合物的方法、含有这些化合物的组合物，以及使用这些化合物进行治疗的方法。