2-O-hexyloxy-3-methoxybenzaldehyde | 97852-83-0

• 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: 2-O-hexyloxy-3-methoxybenzaldehyde
• 英文别名: 2-hexyloxy-3-methoxy-benzaldehyde；2-(Hexyloxy)-3-methoxybenzaldehyde；2-hexoxy-3-methoxybenzaldehyde
• CAS: 97852-83-0
• 化学式: C₁₄H₂₀O₃
• mdl: MFCD00444185
• 分子量: 236.311
• InChiKey: OUFVDIVIENJHSP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  硝基乙烷 、 2-O-hexyloxy-3-methoxybenzaldehyde 在 甲胺 作用下， 生成 2-hexyloxy-1-methoxy-3-(2-nitro-propenyl)-benzene
  参考文献：
  名称：

  Profft, Arzneimittel-Forschung/Drug Research, 1959, vol. 9, p. 157,161

  摘要：

  DOI：

文献信息

• Inhibition of Caco-2 and MCF-7 cancer cells using chalcones: synthesis, biological evaluation and computational study
  作者：Marco Mellado、Mauricio Reyna-Jeldes、Caroline Weinstein-Oppenheimer、Claudio Coddou、Carlos Jara-Gutierrez、Joan Villena、Luis F. Aguilar

  DOI：10.1080/14786419.2021.1984465

  日期：2022.9.2

  development of novel anticancer agents derived from natural sources, like chalcone derivatives. For this investigation, twenty-three chalcones (4a-w) were synthesized and evaluated as antiproliferative agents against MCF-7 and Caco-2 cells, finding three and two compounds with similar or higher antiproliferative activity than daunorubicin, while only two chalcones showed better selectivity indexes than

  摘要 癌症是全球第二大死亡原因，其中乳腺癌和结肠癌是最常见的类型。传统的治疗策略有几个副作用，这些副作用激发了从天然来源（如查尔酮衍生物）中提取的新型抗癌剂的开发。在这项研究中，合成了 23 种查尔酮 ( 4a-w )，并对其作为抗 MCF-7 和 Caco-2 细胞的抗增殖剂进行了评估，发现三种和两种化合物具有与柔红霉素相似或更高的抗增殖活性，而只有两种查尔酮表现出更好的抗增殖活性在 MCF-7 上的选择性指数高于柔红霉素。根据这些结果，我们开发了性能良好的 QSAR 模型 (r > 0.850, q 2>0.650），发现了几个可以改变查尔酮活性和选择性的结构特征。根据这些模型，查尔酮4w和4t分别对 Caco-2 和 MCF-7 具有高效力和选择性，这使得它们成为开发 ROS 非依赖性促凋亡剂的潜在候选药物。
• Fused pyrimidine derivatives as TRPV3 modulators
  申请人：Glenmark Pharmaceuticals, S.A.

  公开号：US08349846B2

  公开（公告）日：2013-01-08

  The present invention related to fused pyrimidine derivatives, which are useful as Transient Receptor Potential Vanilloid 3 (TRPV3) receptors, methods of treating diseases, disorders, conditions modulated by TRPV3. The present invention having the formula (I) and its pharmaceutically acceptable salts thereof, and its processes thereof, wherein all variables are as described herein.

  本发明涉及熔合嘧啶衍生物，其作为瞬时受体电位香草受体3（TRPV3）受体有用，用于治疗由TRPV3调节的疾病，紊乱和状况的方法。本发明具有式（I）及其药学上可接受的盐和其制备方法，其中所有变量如本文所述。
• Fused Pyrimidine Derivatives as Trpv3 Modulators
  申请人：Lingam V S, Prasadarao

  公开号：US20100292254A1

  公开（公告）日：2010-11-18

  The present invention related to fused pyrimidine derivatives, which are useful as Transient Receptor Potential Vanilloid 3 (TRPV3) receptors, methods of treating deseases, disorders, conditions modulated by TRPV3. The present invention having the formula (I) and its pharmaceutically acceptable salts thereof, and its processes thereof, wherein all variables are as described herein.

  本发明涉及熔合嘧啶衍生物，其可用作瞬时受体电位香草酸3（TRPV3）受体，用于治疗由TRPV3调节的疾病，疾病和状况的方法。本发明具有公式（I）及其药学上可接受的盐及其过程，其中所有变量如本文所述。
• Synthesis of chalcones with antiproliferative activity on the SH-SY5Y neuroblastoma cell line: Quantitative Structure–Activity Relationship Models
  作者：Marco Mellado、Alejandro Madrid、Mauricio Reyna、Caroline Weinstein-Oppenheimer、Jaime Mella、Cristian O. Salas、Elizabeth Sánchez、Mauricio Cuellar

  DOI：10.1007/s00044-018-2245-2

  日期：2018.12

  Chalcones are a group of molecules with a broad spectrum of biological activities, being especially appealing for their antiproliferative effects on several cancer cell lines. For this reason, we synthesized 23 chalcones with good to excellent yields and assessed their effect on the viability of the SH-SY5Y neuroblastoma cell line and on primary human fibroblasts. The results indicated that 18 of these compounds were more active than 5-fluorouracil in the cancer cell line and one of them was more selective than this reference drug. To identify structural features related to the antiproliferative activity of these compounds, as well as, the selectivity on the cancer cell line, a 2D-QSAR analysis was performed. The QSAR model (q(2)=0.803; r(2)=0.836) showed that lipophilicity (CLogP) is the most important factor to increase their cytotoxicity on the cancer cell line. On the other hand, the selectivity QSAR model (q(2)=0.917; r(2)=0.916) showed that changes in the Mulliken's charge of the carbonyl group and at the C4' position in the chalcone core can increase the selectivity for SH-SY5Y cell line compared to normal fibroblasts.
• FUSED PYRIMIDINE DERIVATIVES AS TRPV3 MODULATORS
  申请人：Glenmark Pharmaceuticals S.A.

  公开号：EP2229388A2

  公开（公告）日：2010-09-22