3,5-dimethoxy-4-propargyloxybenzaldehyde | 552311-69-0

• 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: 3,5-dimethoxy-4-propargyloxybenzaldehyde
• 英文别名: 3,5-dimethoxy-4-prop-2-ynyloxybenzaldehyde；3,5-dimethoxy-4-prop-2-ynoxybenzaldehyde
• CAS: 552311-69-0
• 化学式: C₁₂H₁₂O₄
• 分子量: 220.225
• InChiKey: QEOIMZXUSQTDMF-UHFFFAOYSA-N

物化性质

• 熔点：
  108-109 °C
• 沸点：
  359.0±42.0 °C(Predicted)
• 密度：
  1.159±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,5-dimethoxy-4-propargyloxybenzaldehyde 在 sodium tetrahydroborate 、 copper(l) iodide 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  双支[3]轮烷中两个荧光团之间的高效分子内能量转移

  摘要：

  设计并研究了一个双支的[3]轮烷，两个[2]轮烷的臂由一个低聚对苯撑亚乙烯基（OPV）荧光团隔开。采用difluoroboradiaza-每个[2]轮烷臂小号-indacene（BODIPY）染料官能化的二苯并[24]冠8大环互锁到在杆部的二苄。证实了[3]轮烷的化学结构，并由1 H和13表征C NMR光谱和高分辨率ESI质谱。通过紫外/可见吸收，荧光和时间分辨荧光光谱研究了[3]轮烷及其参考体系的光物理性质。[3]轮烷的有效能量转移过程是从OPV供体到BODIPY受体发生的，这是因为BODIPY部分的吸收光谱与OPV荧光团的发射光谱之间存在很大的重叠。这表明该系统在设计功能分子系统方面的重要潜力。

  DOI：

  10.1002/asia.201402789
• 作为产物：
  描述：

  3,4,5-三甲氧基苯甲酸甲酯 在 六甲基磷酰三胺 、 lithium aluminium tetrahydride 、 sodium hydride 、 potassium carbonate 、 苯硫酚 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 、 甲苯 为溶剂， 生成 3,5-dimethoxy-4-propargyloxybenzaldehyde
  参考文献：
  名称：

  Design, synthesis, and SAR analysis of cytotoxic sinapyl alcohol derivatives

  摘要：

  Five series totalling 51 of sinapyl alcohol derivatives were designed and synthesized. Their cytotoxicity analyses were performed oil six human tumor cell lines Such as PC-3. CNE, KB, A549, BEL-7404, and HeLa. Certain sinapyl alcohol derivatives showed significant cytotoxic activities. Compound 14d exhibited especially potent cytotoxicity against the BEL-7404 cell line with an IC50 value of 0.7 mu M, which showed more cytotoxic activity than the positive control, cisplatin. The structure-cytotoxicity relationships were discussed and the CoMFA analysis was performed using the cytotoxic data against HeLa cells as a template. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.10.056

文献信息

• BIS(ARYLMETHYLIDENE)ACETONE COMPOUND, ANTI-CANCER AGENT, CARCINOGENESIS-PREVENTIVE AGENT, INHIBITOR OF EXPRESSION OF Ki-Ras, ErbB2, c-Myc AND CYCLINE D1, BETA-CATENIN-DEGRADING AGENT, AND p53 EXPRESSION ENHANCER
  申请人：Shibata Hiroyuki

  公开号：US20100152493A1

  公开（公告）日：2010-06-17

  It has been demanded to improve the poor solubility of curcumin to develop an anti-tumor compound capable of inhibiting the growth of various cancer cells at a low concentration. Thus, disclosed is a novel synthetic compound, a bis(arylmethylidene)acetone, which has both of an excellent anti-tumor activity and a chemo-preventive activity. A bis(arylmethylidene)acetone (i.e., a derivative having a curcumin skeleton) which is an anti-tumor compound and has a chemo-preventive activity is synthesized and screened. A derivative having enhanced anti-tumor activity and chemo-preventive activity can be synthesized.

  要改善姜黄素的溶解度，以开发一种能够在低浓度下抑制各种癌细胞生长的抗肿瘤化合物。因此，披露了一种新型合成化合物，双(芳基甲基亚乙酮)，具有优异的抗肿瘤活性和化学预防活性。合成并筛选了一种双(芳基甲基亚乙酮)（即具有姜黄素骨架的衍生物），它是一种抗肿瘤化合物并具有化学预防活性。可以合成具有增强抗肿瘤活性和化学预防活性的衍生物。
• A bifunctionalized [3]rotaxane and its incorporation into a mechanically interlocked polymer
  作者：Yi Jiang、Jia-Bin Guo、Chuan-Feng Chen

  DOI：10.1039/c0cc00999g

  日期：——

  A novel bifunctionalized [3]rotaxane based on a triptycene-derived macrotricyclic host was conveniently synthesized. On the basis of the [3]rotaxane, a linear main-chain poly[3]rotaxane was further obtained by the highly efficient Huisgen 1,3-dipolar cycloaddition.

  一种基于三苯并环庚烷衍生的大三环主客体的独特双功能化[3]轮烷被便捷地合成。在此基础上，通过高效的Huisgen 1,3-偶极环加成反应，进一步获得了线性主链聚[3]轮烷。
• Discovery and biological evaluation of some (1H-1,2,3-triazol-4-yl)methoxybenzaldehyde derivatives containing an anthraquinone moiety as potent xanthine oxidase inhibitors
  作者：Ting-jian Zhang、Song-ye Li、Wei-yan Yuan、Qing-xia Wu、Lin Wang、Su Yang、Qi Sun、Fan-hao Meng

  DOI：10.1016/j.bmcl.2017.01.049

  日期：2017.2

  A series of (1H-1,2,3-triazol-4-yl)methoxybenzaldehyde derivatives containing an anthraquinone moiety were synthesized and identified as novel xanthine oxidase inhibitors. Among them, the most promising compounds 1h and 1k were obtained with IC50 values of 0.6 μM and 0.8 μM, respectively, which were more than 10-fold potent compared with allopurinol. The Lineweaver-Burk plot revealed that compound

  合成了一系列含有蒽醌部分的（1 H -1,2,3-三唑-4-基）甲氧基苯甲醛衍生物，并将其鉴定为新型黄嘌呤氧化酶抑制剂。其中，获得最有前途的化合物1h和1k的IC 50值分别为0.6μM和0.8μM，与别嘌呤醇相比，具有50倍以上的效力。Lineweaver-Burk图显示化合物1h充当了混合型黄嘌呤氧化酶抑制剂。SAR分析表明，对于抑制效力，苯甲醛部分比蒽醌部分起着更重要的作用。黄嘌呤氧化酶被1h显着抑制的基础 通过分子模型研究合理化。
• Bis(arylmethylidene)acetone compound, anti-cancer agent, carcinogenesis-preventive agent, inhibitor of expression of Ki-Ras, ErbB2, c-Myc and Cycline D1, β-catenin-degrading agent, and p53 expression enhancer
  申请人：National University Corporation Tohoku University

  公开号：US08178727B2

  公开（公告）日：2012-05-15

  It has been demanded to improve the poor solubility of curcumin to develop an anti-tumor compound capable of inhibiting the growth of various cancer cells at a low concentration. Thus, disclosed is a novel synthetic compound, a bis(arylmethylidene)acetone, which has both of an excellent anti-tumor activity and a chemo-preventive activity. A bis(arylmethylidene)acetone (i.e., a derivative having a curcumin skeleton) which is an anti-tumor compound and has a chemo-preventive activity is synthesized and screened. A derivative having enhanced anti-tumor activity and chemo-preventive activity can be synthesized.

  要求改善姜黄素的溶解度以开发一种能够在低浓度下抑制各种癌细胞生长的抗肿瘤化合物。因此，披露了一种新型合成化合物，即双(芳基甲基亚乙酮)，它既具有优异的抗肿瘤活性，又具有预防化学治疗的活性。合成并筛选了一种双(芳基甲基亚乙酮)(即具有姜黄素骨架的衍生物)，它是一种抗肿瘤化合物，具有预防化学治疗的活性。可以合成具有增强抗肿瘤活性和预防化学治疗活性的衍生物。
• A New Naphthopyran Derivative Combines <i>c</i>-Myb Inhibition, Microtubule-Targeting Effects, and Antiangiogenic Properties
  作者：Leonhard H. F. Köhler、Sebastian Reich、Maria Yusenko、Karl-Heinz Klempnauer、Amin H. Shaikh、Khursheed Ahmed、Gerrit Begemann、Rainer Schobert、Bernhard Biersack

  DOI：10.1021/acsmedchemlett.2c00403

  日期：2022.11.10

  three-component reaction of 1-naphthol, and various aryl aldehydes and malononitrile and screened for their c-Myb inhibitory activities. 1b also served as a lead compound for seven new naphthopyran derivatives (3a–f), which were cytotoxic with nanomolar IC50 values, to inhibit the polymerization of tubulin, and to destabilize microtubules in living cells. Especially, the alkyne 3f, originally made for

  基于有前途的c -Myb抑制剂1b，一系列2-氨基-4-芳基-4H-萘并[1,2- b ]吡喃-3-甲腈（1a，2a - q，3a - g）被重新利用或通过1-萘酚、各种芳基醛和丙二腈的三组分反应新合成并筛选其c -Myb抑制活性。1b还充当七种新型萘并吡喃衍生物 ( 3a – f ) 的先导化合物，这些衍生物具有纳摩尔 IC 50值的细胞毒性，可抑制微管蛋白的聚合，并使活细胞中的微管不稳定。特别是，最初使用点击化学进行细胞内定位研究的炔3f在所有进行的测定中都显示出整体高活性。检测到强烈的 G2/M 细胞周期停滞，通过效应器 caspase 3 和 7 的诱导，导致亚 G1 细胞明显增加。在体外和体内均证实了血管生成的抑制作用。总之，3f被发现是一种对癌细胞具有高选择性的多效性化合物，结合了c- Myb抑制、微管不稳定和抗血管生成作用。