3-methoxy-4-methylphenylacetaldehyde | 122333-98-6

• 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: 3-methoxy-4-methylphenylacetaldehyde
• 英文别名: 2-(3-Methoxy-4-methylphenyl)acetaldehyde；2-(3-methoxy-4-methylphenyl)acetaldehyde
• CAS: 122333-98-6
• 化学式: C₁₀H₁₂O₂
• 分子量: 164.204
• InChiKey: BQKGVXOLUUTAIJ-UHFFFAOYSA-N

物化性质

• 沸点：
  261.8±25.0 °C(Predicted)
• 密度：
  1.027±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  3-methoxy-4-methylphenylacetaldehyde 、 乙氧甲酰基亚甲基三苯基膦 以 苯 为溶剂， 反应 2.0h， 以95%的产率得到ethyl 4-(3-methoxy-4-methylphenyl)-2-butenoate
  参考文献：
  名称：

  Introduction of a putative dopaminergic prodrug moiety into a 6,7-substitution pattern characteristic of certain 2-aminotetralin dopaminergic agonists

  摘要：

  On the basis of the premise that the dopaminergic agonist profile of 2-(di-n-propylamino)-5-hydroxy-6-methyltetralin (1a) is due to in vivo oxidation of the 6-methyl moiety and that 1a may represent a novel prodrug strategy, the vicinal methyl-hydroxyl substitution pattern was incorporated into the 6- and 7-positions of 2-(di-n-propylamino)tetralin to give the 6-methyl-7-hydroxy and 6-hydroxy-7-methyl isomers 8 and 9, respectively. A multistep synthetic approach was devised which permitted preparation of target molecules 8 and 9. Pharmacological data revealed that both target compounds exhibit modest dopamine-like effects in the cardioaccelerator nerve assay in the cat, but neither appeared to be metabolically activated as was the case with 1a. The effects of 9 (but not of 8) were antagonized by pretreatment with haloperidol. Thus, the 5-hydroxy-6-methyl substitution pattern in the 2-aminotetralins remains unique as a dopaminergic agonist prodrug structure.

  DOI：

  10.1021/jm00129a029
• 作为产物：
  描述：

  3-甲氧基-4-甲基苯甲醛 在 水 、 sodium methylate 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成 3-methoxy-4-methylphenylacetaldehyde
  参考文献：
  名称：

  Introduction of a putative dopaminergic prodrug moiety into a 6,7-substitution pattern characteristic of certain 2-aminotetralin dopaminergic agonists

  摘要：

  On the basis of the premise that the dopaminergic agonist profile of 2-(di-n-propylamino)-5-hydroxy-6-methyltetralin (1a) is due to in vivo oxidation of the 6-methyl moiety and that 1a may represent a novel prodrug strategy, the vicinal methyl-hydroxyl substitution pattern was incorporated into the 6- and 7-positions of 2-(di-n-propylamino)tetralin to give the 6-methyl-7-hydroxy and 6-hydroxy-7-methyl isomers 8 and 9, respectively. A multistep synthetic approach was devised which permitted preparation of target molecules 8 and 9. Pharmacological data revealed that both target compounds exhibit modest dopamine-like effects in the cardioaccelerator nerve assay in the cat, but neither appeared to be metabolically activated as was the case with 1a. The effects of 9 (but not of 8) were antagonized by pretreatment with haloperidol. Thus, the 5-hydroxy-6-methyl substitution pattern in the 2-aminotetralins remains unique as a dopaminergic agonist prodrug structure.

  DOI：

  10.1021/jm00129a029

文献信息

• [EN] INHIBITORS OF NHE-MEDIATED ANTIPORT<br/>[FR] INHIBITEURS D'ANTIPORT À MÉDIATION PAR NHE
  申请人：ARDELYX INC

  公开号：WO2018129557A1

  公开（公告）日：2018-07-12

  The present disclosure is directed to compounds (Ι') and to their use in methods for the treatment of disorders associated with fluid retention or salt overload, such as heart failure (in particular, congestive heart failure), chronic kidney disease, end-stage renal disease, liver disease, and peroxisome proliferator-activated receptor (PPAR) gamma agonist-induced fluid retention. The present disclosure is also directed to compounds (Ι') and their use in methods for the treatment of hypertension. The present disclosure is also directed to compounds (Ι') and to their use in methods for the treatment of gastrointestinal tract disorders, including the treatment or reduction of pain associated with gastrointestinal tract disorders.

  本公开涉及化合物(Ι')及其在治疗与液体潴留或盐超负荷相关的疾病的方法中的用途，例如心力衰竭（尤其是充血性心力衰竭）、慢性肾病、终末期肾病、肝病以及过氧化物酶体增殖物激活受体（PPAR）gamma激动剂引起的液体潴留。本公开还涉及化合物(Ι')及其在治疗高血压的方法中的用途。本公开还涉及化合物(Ι')及其在治疗胃肠道疾病的方法中的用途，包括治疗或减少与胃肠道疾病相关的疼痛。
• NOVEL COMPOUND OR PHARMACEUTICALLY ACCEPTABLE SALT THEREOF, AND PHARMACEUTICAL COMPOSITION CONTAINING SAME AS ACTIVE INGREDIENT
  申请人：SNU R&DB FOUNDATION

  公开号：US20150183797A1

  公开（公告）日：2015-07-02

  The present invention relates to a compound inhibiting Hsp90 and a pharmaceutical composition comprising the same as an active ingredient. The compounds represented by formula 1 and formula 2 of the present invention suppress the expression of Hsp90 so that they can inhibit the accumulation of HIF-1α, the Hsp90 client protein, and also efficiently inhibit the activation of VEGF. In addition, these compounds display low cytotoxicity, so that they can be effectively used as an active ingredient of an anti-cancer agent, a diabetic retinopathy treating agent, and an anti-arthritic agent.

  本发明涉及一种抑制Hsp90的化合物以及包含其作为活性成分的药物组合物。本发明的化合物1和化合物2所代表的化合物抑制Hsp90的表达，从而能够抑制HIF-1α（Hsp90客户蛋白）的积累，并且有效抑制VEGF的活化。此外，这些化合物显示出低细胞毒性，因此它们可以有效地用作抗癌剂、糖尿病视网膜病变治疗剂和抗关节炎剂的活性成分。
• INHIBITORS OF NHE-MEDIATED ANTIPORT
  申请人：Ardelyx, Inc.

  公开号：EP3565811A1

  公开（公告）日：2019-11-13
• THIADIAZINE DERIVATIVES
  申请人：Richter Gedeon Nyrt.

  公开号：EP3820865A1

  公开（公告）日：2021-05-19
• US9745280B2
  申请人：——

  公开号：US9745280B2

  公开（公告）日：2017-08-29