dihydroisocordoin | 55716-90-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: dihydroisocordoin
• 英文别名: 1-[2,4-Dihydroxy-3-(3-methylbut-2-enyl)phenyl]-3-phenylpropan-1-one；1-[2,4-dihydroxy-3-(3-methylbut-2-enyl)phenyl]-3-phenylpropan-1-one
• CAS: 55716-90-0
• 化学式: C₂₀H₂₂O₃
• 分子量: 310.393
• InChiKey: ZNDLKFYDBGZDRM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-溴-2-丁烯 、 dihydroisocordoin 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 6.0h， 以87.5%的产率得到1-[4-(crotyloxy)-2-hydroxy-3-(prenyl)phenyl]-3-phenylpropan-1-one
  参考文献：
  名称：

  Synthesis of dihydroisorcordoin derivatives and their in vitro anti-oomycete activities

  摘要：

  A series of novel dihydrochalcone derivatives 2-7 were synthesized from dihydroisorcordoin 1 which was isolated from the aerial parts of Adesmia balsamica. The structures of all compounds were confirmed by H-1 NMR, C-13 NMR, and HRMS. Their anti-oomycete activity was evaluated in vitro against Saprolegnia parasitica and Saprolegnia diclina. Some of the newly synthesized compounds exhibited better anti-oomycete activities at low values compared with bronopol and fluconazole as positive controls. Among them, compound 7 exhibited strong activity, with minimum inhibitory concentration and minimum oomyceticidal concentration values of 75 and 100 mu g/mL, respectively.[GRAPHICS].

  DOI：

  10.1080/14786419.2018.1460828

文献信息

• Semi-Synthesis of Dihydrochalcone Derivatives and Their<i>in Vitro</i>Antimicrobial Activities
  作者：Maurice Awouafack、Souvik Kusari、Marc Lamshöft、Dieudonne Ngamga、Pierre Tane、Michael Spiteller

  DOI：10.1055/s-0029-1240619

  日期：2010.4

  We describe the semi-synthesis of dihydrochalcone derivatives and their in vitro antimicrobial activities. These compounds were prepared by modifying two naturally occurring antimicrobial dihydrochalcones, erioschalcones A and B, reported by us earlier. The structures of the compounds were assigned on the basis of spectroscopic evidence and by comparing their physical and spectroscopic data with those reported in the literature. All the compounds were subjected to in vitro antimicrobial assays against a panel of pathogenic microorganisms, including gram-positive and gram-negative bacteria, and fungi. The antimicrobial efficacies of this class of compounds were established by correlating the activity profile of each compound with its structure and by comparing the activities of all the compounds with each other based on their structure. This should enable the development of other derivatives of the dihydrochalcone family that would serve as more potent antimicrobial agents against specific pathogens.

  我们介绍了二氢查尔酮衍生物的半合成及其体外抗菌活性。这些化合物是通过对我们早先报道的两种天然抗菌二氢查耳酮（erioschalcones A 和 B）进行改良而制备的。这些化合物的结构是根据光谱证据并将其物理和光谱数据与文献报道的数据进行比较后确定的。对所有化合物都进行了体外抗菌试验，试验对象是一组病原微生物，包括革兰氏阳性菌、革兰氏阴性菌和真菌。通过将每个化合物的活性特征与其结构相关联，并根据其结构比较所有化合物的活性，确定了这一类化合物的抗菌功效。这将有助于开发二氢查尔酮家族的其他衍生物，使其成为针对特定病原体的更有效的抗菌剂。
• Anti-inflammatory and anti-hypersensitive effects of the chalcone isocordoin and its semisynthetic derivatives in mice
  作者：Gislaine Francieli Da Silva、Fátima De Campos Buzzi、José Roberto Santin、Alejandro Yam-Puc、Fabiola Escalante-Erosa、Karlina-García Sosa、Luiz Carlos Klein、Luis Manuel Peña Rodriguez、Valdir Cechinel Filho、Nara Lins Meira Quintão

  DOI：10.1097/fbp.0000000000000577

  日期：2020.12

  from different plants, has been found to present a range of interesting biological properties. This study aimed to evaluate the anti-hypersensitive and anti-inflammatory effects of isocordoin (1) and several natural and semisynthetic derivatives (2–10). Initial evaluation of (1), dihydroisocordoin (2) and six semisynthetic derivatives (3–8) in the inhibition of abdominal writhes induced by acetic acid

  Isocordoin (1) 是一种从不同植物中分离出来的查耳酮，已被发现具有一系列有趣的生物学特性。本研究旨在评估异考多因 (1) 和几种天然和半合成衍生物 (2-10) 的抗过敏和抗炎作用。对 (1)、二氢异香豆素 (2) 和六种半合成衍生物 (3-8) 抑制醋酸模型引起的腹部扭动的初步评估表明，只有异香豆素二甲醚 (5) 引起超过 70% 的抑制。对 5 的抗水肿活性和抗过敏作用的进一步评估由角叉菜胶、脂多糖 (LPS)、缓激肽 (BK)、前列腺素 E2 (PGE2) 和肾上腺素引起，结果表明异科尔多因二甲醚 (5) 对角叉菜胶具有离散抑制作用- 和 LPS 诱导的超敏反应，和角叉菜胶引起的爪子水肿，并且它能够显着减少 BK 引起的水肿和超敏反应。此外，当在 PGE2 模型中测试时，5 只干扰爪子水肿，对爪子超敏反应没有任何影响。在 BK 诱导的水肿和超敏反应中对天然异科尔多因 (1)
• Cytotoxic potential of dihydrochalcones from <i>Eriosema glomeratum</i> and their semi-synthetic derivatives
  作者：Gaétan Tchangou Tabakam、Takeshi Kodama、Marthe Aimée Tchuente Tchuenmogne、Nhat Nam Hoang、Battsengel Nomin-Erdene、Silvère Augustin Ngouela、Mathieu Tene、Hiroyuki Morita、Maurice Ducret Awouafack

  DOI：10.1080/14786419.2022.2111563

  日期：——

  In the search of cytotoxic dihydrochalcones, this investigation led to the isolation of seven compounds (1-7) from Eriosema glomeratum and the preparation of eight derivatives (8-15). The cytotoxic...

  在寻找细胞毒性二氢查耳酮的过程中，这项研究从 Eriosema glomeratum 中分离出七种化合物 (1-7) 并制备了八种衍生物 (8-15)。细胞毒性...
• Synthesis of dihydroisorcordoin derivatives and their <i>in vitro</i> anti-oomycete activities
  作者：Iván Montenegro、Alejandro Madrid

  DOI：10.1080/14786419.2018.1460828

  日期：2019.4.18

  A series of novel dihydrochalcone derivatives 2-7 were synthesized from dihydroisorcordoin 1 which was isolated from the aerial parts of Adesmia balsamica. The structures of all compounds were confirmed by H-1 NMR, C-13 NMR, and HRMS. Their anti-oomycete activity was evaluated in vitro against Saprolegnia parasitica and Saprolegnia diclina. Some of the newly synthesized compounds exhibited better anti-oomycete activities at low values compared with bronopol and fluconazole as positive controls. Among them, compound 7 exhibited strong activity, with minimum inhibitory concentration and minimum oomyceticidal concentration values of 75 and 100 mu g/mL, respectively.[GRAPHICS].