4-methoxy-3-(4-methylpiperazin-1-ylmethyl)benzaldehyde | 932893-60-2

• 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: 4-methoxy-3-(4-methylpiperazin-1-ylmethyl)benzaldehyde
• 英文别名: 4-Methoxy-3-[(4-methylpiperazin-1-yl)methyl]benzaldehyde
• CAS: 932893-60-2
• 化学式: C₁₄H₂₀N₂O₂
• mdl: MFCD10485469
• 分子量: 248.325
• InChiKey: KZLZFTWBOPLJSN-UHFFFAOYSA-N

物化性质

• 沸点：
  372.8±42.0 °C(Predicted)
• 密度：
  1.115±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  32.8
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933599090

反应信息

• 作为反应物：
  描述：

  4-methoxy-3-(4-methylpiperazin-1-ylmethyl)benzaldehyde 、 2'-hydroxy-5'-uracilylmethylacetophenone 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以54%的产率得到3-(N-methylpiperazinyl-1)methyl-2'-hydroxy-4-methoxy-5'-uracilylmethylchalcone
  参考文献：
  名称：

  New Chalcones Containing Nucleosides Exhibiting In Vitro Anti-cancer Activities

  摘要：

  21 个新查耳酮 9a-m（不包括 9e、9j 和 9l）和 10a-m（不包括 10j 和 10l），含有核碱基 由2'-羟基苯乙酮(1)通过氯甲基化、亲核化等反应合成 胸腺嘧啶和尿嘧啶取代，以及克莱森-施密特反应。对这些新查耳酮进行了体外细胞毒性评估 针对五种人类癌细胞系：SK-LU-1、Hep-G2、MCF7、SW480 和 P388。结果表明 大多数测试的查耳酮对除 10h 和 10i 之外的五种癌细胞系均表现出抑制活性。其中 合成的查耳酮中，化合物 10c 对 MCF-7、SK-LU-1、SW480、HepG2 和 P388 的 IC50 值分别为 4.42、4.81、5.27、3.67 和 4.11μg/mL。

  DOI：

  10.2174/1570178611666140401221121
• 作为产物：
  描述：

  3-甲酰基-4-甲氧基苯甲酸甲酯 在 manganese(IV) oxide 、 lithium aluminium tetrahydride 、 三乙酰氧基硼氢化钠 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 15.0h， 生成 4-methoxy-3-(4-methylpiperazin-1-ylmethyl)benzaldehyde
  参考文献：
  名称：

  Synthesis and in Vitro Anticancer Activity of the First Class of Dual Inhibitors of REV-ERBβ and Autophagy

  摘要：

  Autophagy inhibition is emerging as a promising anticancer strategy. We recently reported that the circadian nuclear receptor REV-ERB beta plays an unexpected role in sustaining cancer cell survival when the autophagy flux is compromised. We also identified 4-[[[1-(2-fluorophenyl)cyclopentynamino]methyl]-2-[(4-methylpiperazin-1-yl)methyl]phenol, 1 (ARN5187), as a novel dual inhibitor of REV-ERB beta and autophagy. 1 had improved cytotoxicity against BT-474 breast cancer cells compared to chloroquine, a clinically relevant autophagy inhibitor. Here, we present the results of structure activity studies, based around 1, that disclose the first class of dual inhibitors of REV-ERB beta and autophagy. This study led to identification of 18 and 28, which were more effective REV-ERB beta antagonists than 1 and were more cytotoxic to BT-474. The combination of optimal chemical and structural moieties of these analogs generated 30, which elicited 15-fold greater REV-ERB beta inhibitory and cytotoxic activities compared to 1. Furthermore, 30 induced death in a panel of tumor cell lines at doses 5-50 times lower than an equitoxic amount of chloroquine but did not affect the viability of normal mammary epithelial cells.

  DOI：

  10.1021/acs.jmedchem.5b00511

文献信息

• DIARYLALKYLAMINE REV-ERB ANTAGONISTS AND THEIR USE AS MEDICAMENTS
  申请人：FONDAZIONE ISTITUTO ITALIANO DI TECNOLOGIA

  公开号：US20160237057A1

  公开（公告）日：2016-08-18

  The present invention relates to compounds of Formula (I) or pharmaceutically acceptable salts or solvates thereof: It further discloses a pharmaceutical composition comprising the compounds of Formula (I) and their uses as anti-proliferative and pro-apoptotic agents for cancer therapy.

  本发明涉及式（I）的化合物或其药学上可接受的盐或溶剂：它进一步揭示了包含式（I）化合物的制药组合物以及它们作为抗增殖和促凋亡剂用于癌症治疗的用途。
• Anti-fibrotic compounds
  申请人：Certa Therapeutics Pty Ltd

  公开号：US11014873B2

  公开（公告）日：2021-05-25

  Provided herein are anti-fibrotic compounds, in particular those of Formula (I), that inhibit the TGF-beta signaling pathway. Also provided are pharmaceutical compositions comprising the anti-fibrotic compounds, and methods of treating diseases or conditions associated with fibrosis, inflammation, and benign or malignant neoplastic diseases in a subject by administering a compound or composition described herein. (Formula (I))

  本文提供了抑制 TGF-beta 信号通路的抗纤维化化合物，特别是式（I）化合物。还提供了包含抗纤维化化合物的药物组合物，以及通过施用本文所述化合物或组合物治疗受试者与纤维化、炎症、良性或恶性肿瘤疾病相关的疾病或病症的方法。式（I
• [EN] ANTI-FIBROTIC COMPOUNDS<br/>[FR] COMPOSÉS ANTI-FIBROTIQUES
  申请人：CERTA THERAPEUTICS PTY LTD

  公开号：WO2018144620A9

  公开（公告）日：2019-01-24
• Synthesis and antimicrobial activity of chalcones containing benzotriazolylmethyl and imidazolylmethyl substituents
  作者：L. V. Chinh、T. N. Hung、N. T. Nga、T. T. N. Hang、T. T. N. Mai、V. A. Tarasevich

  DOI：10.1134/s1070428014120094

  日期：2014.12

  Methods have been developed for the synthesis of new 1H-benzotriazol-1-ylmethyl- and 1H-imidazol-1-ylmethyl-substituted chalcones starting from 2-hydroxyacetophenone. The procedures include chloromethylation, N-alkylation, and Claisen-Schmidt condensation. The presence of an imidazole fragment on the ring A and piperazine fragment on the ring B of the resulting chalcones increases their antimicrobial activity (minimum inhibitory concentration 12.5-50.0 mu g/mL), whereas introduction of a benzotriazole fragment reduces the antimicrobial activity.
• ANTI-FIBROTIC COMPOUNDS
  申请人：Certa Therapeutics Pty Ltd

  公开号：US20200055814A1

  公开（公告）日：2020-02-20

  Provided herein are anti-fibrotic compounds, in particular those of Formula (I), that inhibit the TGF-beta signaling pathway. Also provided are pharmaceutical compositions comprising the anti-fibrotic compounds, and methods of treating diseases or conditions associated with fibrosis, inflammation, and benign or malignant neoplastic diseases in a subject by administering a compound KIN or composition described herein. (Formula (I))