5-prenylvanillin | 18423-13-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 5-prenylvanillin
• 英文别名: 4-Hydroxy-3-methoxy-5-(3-methyl-2-buten-1-yl)benzaldehyde；4-hydroxy-3-methoxy-5-(3-methylbut-2-enyl)benzaldehyde
• CAS: 18423-13-7
• 化学式: C₁₃H₁₆O₃
• 分子量: 220.268
• InChiKey: CKJCGNYKNJFKLA-UHFFFAOYSA-N

物化性质

• 沸点：
  350.3±42.0 °C(Predicted)
• 密度：
  1.105±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 储存条件：
  存储条件：2-8°C，干燥且密封。

反应信息

• 作为反应物：
  描述：

  5-prenylvanillin 在 polystyrene-based selenenyl bromide resin 、 双氧水 作用下， 以 二氯甲烷 、 四氢呋喃 为溶剂， 反应 0.66h， 生成 6-Formyl-8-methoxy-2,2-dimethyl-2H-<1>benzopyran
  参考文献：
  名称：

  基于特权结构的类天然产物组合库。1. 苯并吡喃的一般原理及固相合成

  摘要：

  在此，我们报告了一种基于特权结构原理设计和构建天然和天然产物类库的新策略，该术语最初用于描述能够与各种不相关的分子靶标相互作用的结构基序。讨论了天然产物中此类特权结构的鉴定，随后选择 2,2-二甲基苯并吡喃部分作为通过该策略构建类天然产物库的初始模板。最初，采用独特的环加载策略开发了苯并吡喃基序的新型固相合成，该策略依赖于使用新的聚苯乙烯基溴化硒树脂。一旦确定了这些苯并吡喃的加载、加工和裂解，

  DOI：

  10.1021/ja002033k
• 作为产物：
  描述：

  在 manganese(IV) oxide 作用下， 以 N,N-二甲基苯胺 、 甲苯 为溶剂， 反应 4.5h， 生成 5-prenylvanillin
  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

文献信息

• 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。
• 一种新型姜黄素类似物及其制备方法和应用
  申请人：天津科技大学

  公开号：CN110229056B

  公开（公告）日：2022-11-08

  本发明涉及一种新型姜黄素类似物，所述类似物为使用天然产物中常见的取代基修饰姜黄素得到的，具体地，所述类似物的结构通式为：其中，R1和R2是氢，烯丙基，异戊烯基、香叶基中的一种；或者，所述类似物的结构通式为：其中，R1和R2是氢，烯丙基，异戊烯基、香叶基中的一种。本姜黄素类似物具有较好的抗氧化活性，其制备路线短，合成工艺简单易操作。
• Preparation, characterization, antioxidant evaluation of new curcumin derivatives and effects of forming HSA-bound nanoparticles on the stability and activity
  作者：Tiantian Hao、Kai Wang、Shutong Zhang、Shuyan Yang、Pingxi Wang、Feng Gao、Yufan Zhao、Na Guo、Peng Yu

  DOI：10.1016/j.ejmech.2020.112798

  日期：2020.12

  field since it showed various activities. However, some serious issues limit its application, for example, the extremely low solubility, stability and bioavailability. In this study, 10 Curcumin derivatives were synthesized and characterized by 1H NMR, 13C NMR and HR-MS, then their antioxidant activity was evaluated. Compound 2 and curcumin were further investigated by preparing HSA-bound nanoparticles

  姜黄素（CCM）是一种众所周知的活性成分，由于其具有多种活性，因此已在食品和医药领域进行了广泛的研究。但是，一些严重的问题限制了它的应用，例如，极低的溶解度，稳定性和生物利用度。本研究合成了10种姜黄素衍生物，并通过1 H NMR，13 C NMR和HR-MS对其进行了表征，然后评估了其抗氧化活性。通过制备结合HSA的纳米颗粒（NP-2和NP-CCM），进一步研究了化合物2和姜黄素，以克服上述困难。通过动态光散射（DLS）测量所得的纳米粒子尺寸约为110 nm，即化合物2的稳定性在NP-2中明显增加。首先，NP-2显示出更有效的抗氧化和抗肿瘤活性，这可能归因于2中引入的异戊烯基，认为异戊烯基增加了化合物2与HSA之间的相互作用。总体而言，NP-2在某些食品和药品应用中具有巨大的潜力。
• 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.
• Natural Product-like Combinatorial Libraries Based on Privileged Structures. 2. Construction of a 10 000-Membered Benzopyran Library by Directed Split-and-Pool Chemistry Using NanoKans and Optical Encoding
  作者：K. C. Nicolaou、J. A. Pfefferkorn、H. J. Mitchell、A. J. Roecker、S. Barluenga、G.-Q. Cao、R. L. Affleck、J. E. Lillig

  DOI：10.1021/ja002034c

  日期：2000.10.1

  nonchemical tagging and sorting of library members during split-and-pool synthesis. The overall synthetic strategy for library construction is discussed and the individual reaction pathways are examined in the context of specific library members, illustrating reaction conditions as well as yields and purities. The issues of building block selection and quality control of library members are also addressed

  我们开发了一种可靠且通用的固相策略，用于苯并吡喃模板的天然和设计衍生物的分流合成（见前文），现在我们报告了 10 000 元天然产物类化合物的构建化学生物学研究图书馆。同时，我们报告了 IRORI NanoKan 光学编码系统的早期应用，用于在拆分池合成过程中对文库成员进行高通量非化学标记和分类。讨论了文库构建的整体合成策略，并在特定文库成员的背景下检查了各个反应途径，说明了反应条件以及产量和纯度。图书馆成员的积木选择和质量控制问题也得到解决，最后，