4-(1,1-二甲基-2-丙炔氧基)-3-甲氧基苯甲醛 | 122850-52-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-(1,1-二甲基-2-丙炔氧基)-3-甲氧基苯甲醛
• 英文名称: 3-methoxy-4-((2-methylbut-3-yn-2-yl)oxy)benzaldehyde
• 英文别名: 3-Methoxy-4-(2-methylbut-3-yn-2-yloxy)benzaldehyde
• CAS: 122850-52-6
• 化学式: C₁₃H₁₄O₃
• 分子量: 218.252
• InChiKey: RCVVRNQWSCJYMQ-UHFFFAOYSA-N

物化性质

• 熔点：
  58 °C
• 沸点：
  338.8±32.0 °C(Predicted)
• 密度：
  1.097±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  4-(1,1-二甲基-2-丙炔氧基)-3-甲氧基苯甲醛 在 manganese(IV) oxide 、 sodium tetrahydroborate 、 Lindlar's catalyst 、 氢气 、 三乙胺 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基苯胺 、 甲苯 为溶剂， 反应 5.5h， 生成 3-Methoxy-4-(2-methoxyethoxymethoxy)-5-(3-methylbut-2-enyl)benzaldehyde
  参考文献：
  名称：

  Dissecting the Pharmacophore of Curcumin. Which Structural Element Is Critical for Which Action?

  摘要：

  The dietary phenolic curcumin (1a) is the archetypal network pharmacological agent; but is characterized by an ill-defined pharmacophore. Nevertheless, structure-activity studies of la have mainly focused on a single biological end-point and on a single structural element, the aliphatic his-enoyl moiety. The comparative investigation of more than one end-point of curcumin and the modification of its aromatic region have been largely overlooked. To address these Issues, we have investigated the effect of aromatic C-prenylation in the three archetypal structural types' of curcuminoids namely, curcumin, itself (1a), its truncated analogue 2a (C-5-curcumin), and (as the reduced, isoamyl version) the tetiahydro derivative 3a, comparatively evaluating reactivity with thiols and activity in biochemical (inhibition of NF-kappa B, HIV-1-Tat transactivation, Nrf2 activation) and phenotypic (anti-HIV action) assays sensitive, to a various extent, to thia-Michael addition. Prenylation, a validated maneuver for bioactivity modulation in plant phenolics, had no effect on Michael reactivity but was detrimental for all biological end-points investigated, dissecting thiol trapping from activity, While hydrogenation attenuated, but did not completely abrogate, the activity of 1a. The C-5-curcuminoid 2a outperformed the natural product in all end-points investigated and was identified as a novel high-potency anti-HIV lead in a cellular model of HIV infection. Taken together, these observations show that Michael reactivity is critical element of the curcumin pharmacophore, but also reveal a surprising sensitivity Of bioactivity; to C-prenylation of the vanillyl moiety.

  DOI：

  10.1021/np400148e
• 作为产物：
  描述：

  3-氯-3-甲基-1-丁炔 、 香草醛 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 4.0h， 生成 4-(1,1-二甲基-2-丙炔氧基)-3-甲氧基苯甲醛
  参考文献：
  名称：

  提高 HDAC 抑制剂抗癌作用的新型二氢吡喃吲哚的合成、表征和生物学评价

  摘要：

  从化合物库的初步筛选中，二氢吡喃吲哚支架被确定为提高 HDAC 抑制剂抗癌活性的有希望的目标。已经开发了一种合适的方法，通过 Hemetsberger 吲哚合成使用叠氮苯基丙烯酸酯制备新型二氢吡喃并吲哚，衍生自相应的炔基苯甲醛与叠氮乙酸甲酯的反应，然后在高沸点溶剂中进行热环化。评估了所有新合成化合物对 SH-SY5Y 和 Kelly 神经母细胞瘤细胞以及 MDA-MB-231 和 MCF-7 乳腺癌细胞系的抗癌活性。生物学研究表明，四环系统在较高浓度下对神经母细胞瘤癌细胞具有显着的细胞毒活性。更重要的是，这些系统在较低浓度下显着增强了 SAHA 毒性。除此之外，发现指定系统对健康人体细胞的毒性显着低于癌细胞。

  DOI：

  10.3390/molecules25061377

文献信息

• HYPOXIA INDUCIBLE FACTOR-1 PATHWAY INHIBITORS AND USES AS ANTICANCER AND IMAGING AGENTS
  申请人：EMORY UNIVERSITY

  公开号：US20130164218A1

  公开（公告）日：2013-06-27

  This disclosure relates to Hypoxia Inducible Factor-1 pathway inhibitors and uses as anticancer and imaging agents. In certain embodiments, the disclosure contemplates compounds and pharmaceutical compositions disclosed herein.

  本公开涉及缺氧诱导因子-1通路抑制剂及其作为抗癌和成像剂的用途。在某些实施方式中，本公开考虑了在此披露的化合物和药物组成物。
• The synthesis and evaluation of new benzophenone derivatives as tubulin polymerization inhibitors
  作者：Shun Zhang、Baijiao An、Jun Yan、Ling Huang、Xingshu Li

  DOI：10.1039/c6ra16948a

  日期：——

  Inspired by the potent inhibition activity of phenstatin and millepachine against cancer cell growth, a series of new benzophenone derivatives were synthesized and evaluated as tubulin polymerization inhibitors. Among them, compound 10a exhibited 0.029–0.062 μM of IC50 for five human cancer cell lines, which is much better than that of the two leading compounds. Flow cytometric analysis showed that

  受苯达他汀和米拉帕星对癌细胞生长的有效抑制作用的启发，合成了一系列新的二苯甲酮衍生物并将其作为微管蛋白聚合抑制剂进行评估。其中，化合物10a对五种人类癌细胞系的IC 50值为0.029-0.062μM ，远优于两种主要化合物的IC 50。流式细胞仪分析表明10a诱导A549细胞G2 / M期阻滞和凋亡。细胞研究表明10a诱导的细胞凋亡与线粒体膜电位（MMP）的崩溃有关。总体而言，当前的研究表明，通过靶向微管蛋白，二苯甲酮衍生物是有前途的抗癌药。
• Synthesis and pharmacological properties of naturally occurring prenylated and pyranochalcones as potent anti-inflammatory agents
  作者：Kongara Damodar、Jin-Kyung Kim、Jong-Gab Jun

  DOI：10.1016/j.cclet.2016.01.043

  日期：2016.5

  efficient approach has been developed for the synthesis of naturally occurring prenylated chalcones viz. kanzonol C ( 1 ), stipulin ( 2 ), crotaorixin ( 3 ), medicagenin ( 4 ), licoagrochalcone A ( 5 ) and abyssinone D ( 6 ) along with the pyranochalcones paratocarpin C ( 7 ), anthyllisone ( 8 ) and 3- O -methylabyssinone A ( 9 ). The key step of the synthesis is a Claisen–Schmidt condensation. Subsequently

  摘要已开发出一种有效的方法来合成天然存在的烯丙基查耳酮。坎佐诺尔C（1），链球菌素（2），Crotaorixin（3），药物元素素（4），利加格查尔酮A（5）和Abyssinone D（6）以及吡喃丙酮副棕榈素C（7），蒽醌（8）和3- O。 -甲基杜鹃花A（9）。合成的关键步骤是克莱森-施密特缩合反应。随后，在脂多糖（LPS）诱导的RAW-264.7巨噬细胞中研究了它们的抗炎作用。在合成的查耳酮中，化合物5（IC 50 = 10.41μmol/ L），化合物6（IC 50 = 9.65μmol/ L）和化合物8（IC 50 = 15.34μmol/ L）表现出显着的活性，没有细胞毒性。化合物9（IC 50 = 4.5μmol/ L）表现出最大（83.6％）一氧化氮（NO）抑制作用，但显示出轻微的细胞毒性。
• 프레닐찰콘 및 피라노찰콘 화합물 합성방법
  申请人：Industry Academic Cooperation Foundation, Hallym University 한림대학교 산학협력단(220070195175) BRN ▼221-82-10284

  公开号：KR20170024291A

  公开（公告）日：2017-03-07

  본 발명자들은 클라이젠-슈미트 응축 (Claisen-Schmidt condensation)을 주요 단계로 이용하여 천연 프레닐 찰콘 및 피라노찰콘 화합물 1-9를 합성하는 간단하고 효과적인 방법을 발명하였다. 또한, 합성한 화합물들의 항염증 효과를 지다당으로 자극한 RAW 264.7 대식세포에서 평가하였다. 그 결과, 원환 A (아세토페논 부분)에 프레닐기를 가진 찰콘 화합물은 산화질소 생성에 대해 약한 억제 또는 억제를 나타내지 않은 반면, 원환 A에 프레닐기를 갖지 않은 찰콘 (5, 6, 8 및 9)은 보통 내지는 좋은 활성을 나타내었으며, 세포독성은 없었다.

  The inventors have developed a simple and effective method for synthesizing natural prenyl chalcones and pyranochalcones compounds 1-9 using Claisen-Schmidt condensation as a key step. Furthermore, the anti-inflammatory effects of the synthesized compounds were evaluated on RAW 264.7 macrophage cells stimulated by lipopolysaccharide. As a result, chalcone compounds with prenyl groups on ring A (acetophenone moiety) showed weak inhibition or no inhibition of nitric oxide production, while chalcones without prenyl groups on ring A (5, 6, 8, and 9) exhibited moderate to good activity with no cytotoxicity.
• MICROWAVE ASSISTED SYNTHESIS AND ΑΝΤΙMICROBIAL ACTIVITY OF 2,2-DIMETHYL CHROMENES
  作者：K. Suresh Babu、B. China Raju、B. Praveen、K. Hara Kishore、U. Suryanarayana Murty、J. Madhusudana Rao

  DOI：10.1515/hc.2003.9.5.519

  日期：2003.1