didehydroconicol | 868279-76-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: didehydroconicol
• 英文别名: 6,6,9-trimethyl-6H-dibenzo[b,d]pyran-2-ol；6,6,9-trimethyl-6H-benzo[c]chromen-2-ol；6,6,9-trimethylbenzo[c]chromen-2-ol
• CAS: 868279-76-9
• 化学式: C₁₆H₁₆O₂
• 分子量: 240.302
• InChiKey: AXYGIQAHRDDHJD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  didehydroconicol 生成 3,5-dinitro-benzoic acid-(6,6,9-trimethyl-6H-benzo[c]chromen-2-yl ester)
  参考文献：
  名称：

  205.印度大麻。第三部分 二苯并吡喃衍生物的合成，包括大麻酚的异构体

  摘要：

  DOI：

  10.1039/jr9400001118
• 作为产物：
  描述：

  2',5'-dimethoxy-5-methyl-biphenyl-2-carbonitrile 在 吡啶 、 乙醚 、 氢溴酸 、 苯甲醚 作用下， 生成 didehydroconicol
  参考文献：
  名称：

  205.印度大麻。第三部分 二苯并吡喃衍生物的合成，包括大麻酚的异构体

  摘要：

  DOI：

  10.1039/jr9400001118

文献信息

• SARs for the Antiparasitic Plant Metabolite Pulchrol. 3. Combinations of New Substituents in A/B-Rings and A/C-Rings
  作者：Paola Terrazas、Efrain Salamanca、Marcelo Dávila、Sophie Manner、Alberto Gimenez、Olov Sterner

  DOI：10.3390/molecules26133944

  日期：——

  The natural products pulchrol and pulchral, isolated from the roots of the Mexican plant Bourreria pulchra, have previously been shown to possess antiparasitic activity towards Trypanosoma cruzi, Leishmania braziliensis and L. amazonensis, which are protozoa responsible for Chagas disease and leishmaniasis. These infections have been classified as neglected diseases, and still require the development of safer and more efficient alternatives to their current treatments. Recent SARs studies, based on the pulchrol scaffold, showed which effects exchanges of its substituents have on the antileishmanial and antitrypanosomal activity. Many of the analogues prepared were shown to be more potent than pulchrol and the current drugs used to treat leishmaniasis and Chagas disease (miltefosine and benznidazole, respectively), in vitro. Moreover, indications of some of the possible interactions that may take place in the binding sites were also identified. In this study, 12 analogues with modifications at two or three different positions in two of the three rings were prepared by synthetic and semi-synthetic procedures. The molecules were assayed in vitro towards T. cruzi epimastigotes, L. braziliensis promastigotes, and L. amazonensis promastigotes. Some compounds had higher antiparasitic activity than the parental compound pulchrol, and in some cases even benznidazole and miltefosine. The best combinations in this subset are with carbonyl functionalities in the A-ring and isopropyl groups in the C-ring, as well as with alkyl substituents in both the A- and C-rings combined with a hydroxyl group in position 1 (C-ring). The latter corresponds to cannabinol, which indeed was shown to be potent towards all the parasites.

  墨西哥植物 Bourreria pulchra 的根部中分离出的天然产物 pulchrol 和 pulchral 已被证明具有抗原虫活性，对克氏锥虫、巴西利亚利什曼虫和亚马逊利什曼虫等原虫引起的光谷病和利什曼病具有活性。这些感染已被归类为被忽视的疾病，仍需要开发更安全、更有效的替代治疗方法。最近的结构活性关系研究，基于 pulchrol 结构骨架，展示了其取代基之间交换对抗利什曼虫和抗克氏锥虫活性的影响。许多制备的类似物显示比 pulchrol 和目前用于治疗利什曼病和光谷病的药物（分别为米尔特霉素和苯硝唑）更具有潜力。此外，还发现了可能发生在结合位点中的一些相互作用迹象。在这项研究中，通过合成和半合成方法制备了在两个或三个不同位置的两个三环中进行修饰的12个类似物。这些分子在体外对克氏锥虫的梭形体、巴西利亚利什曼虫的梭形体和亚马逊利什曼虫的梭形体进行了测定。一些化合物的抗原虫活性比母体化合物 pulchrol 更高，甚至有时比苯硝唑和米尔特霉素还要高。在这个子集中效果最好的组合是 A 环中的酮功能基和 C 环中的异丙基，以及 A 和 C 两环中的烷基取代基与位置 1（C 环）的羟基结合。后者对所有寄生虫都显示出了强大的活性，这对应于大麻酚。
• Marine Natural Meroterpenes: Synthesis and Antiproliferative Activity
  作者：Annabel Simon-Levert、Christophe Menniti、Laurent Soulère、Anne-Marie Genevière、Chantal Barthomeuf、Bernard Banaigs、Anne Witczak

  DOI：10.3390/md8020347

  日期：——

  Meroterpenes are compounds of mixed biogenesis, isolated from plants, microorganisms and marine invertebrates. We have previously isolated and determined the structure for a series of meroterpenes extracted from the ascidian Aplidium aff. densum. Here, we demonstrate the chemical synthesis of three of them and their derivatives, and evaluate their biological activity on two bacterial strains, on sea urchin eggs, and on cancerous and healthy human cells.

  Meroterpenes是来自植物、微生物和海洋无脊椎动物的混合生物来源化合物。我们之前已从海鞘Aplidium aff. densum中分离并确定了一系列meroterpenes的结构。在这里，我们展示了三种meroterpenes及其衍生物的化学合成，并评估了它们对两种细菌菌株、海胆卵子以及癌细胞和健康人类细胞的生物活性。
• Synthesis of the Bioactive Benzochromenes Pulchrol and Pulchral, Metabolites of<i>Bourreria pulchra</i>
  作者：Dan Killander、Olov Sterner

  DOI：10.1002/ejoc.201301792

  日期：2014.3

  and few efficient treatments are available. Recently, the two benzochromenes pulchrol (1) and pulchral (2) were reported from the roots of Bourreria pulchra, and especially 1 but also 2 was found to be active towards the parasites. In this paper, we present a total synthesis of 1 and 2 to facilitate their biological evaluation. The synthesis is mild, short, and high yielding and suitable for a structure-activity

  寄生虫 Leshmania mexicana 和 Trypanosoma cruzi 会导致严重的健康问题，并且几乎没有有效的治疗方法。最近，从 Bourreria pulchra 的根中报道了两种苯并色烯 pulchrol (1) 和 pulchral (2)，特别是 1 和 2 被发现对寄生虫有活性。在本文中，我们提出了 1 和 2 的全合成，以促进它们的生物学评估。该合成方法温和、时间短、收率高，适用于构效关系研究。
• Palladium‐Catalyzed Suzuki Coupling and NIS‐Mediated Dehydrogenative Cylcoetherification: A Concise Approach to 6,6‐Disubstituted 6 <i>H</i> ‐benzo[ <i>c</i> ]chromenes and Total Synthesis of Didehydroconicol
  作者：Chander Shekhar、Gedu Satyanarayana

  DOI：10.1002/ejoc.202101444

  日期：2022.5.13

  Herein, we report a concise approach of 6,6-disubstituted 6H-benzo[c]chromenes in a two-step sequence starting from ortho-bromo benzylic alcohols and arylboronic acids, using intermolecular palladium-catalyzed C−C and intramolecular N-Iodosuccinimide (NIS) mediated key C−O bonds construction.

  在此，我们报告了一种从邻溴苯甲醇和芳基硼酸开始的两步序列中 6,6-二取代 6 H-苯并[ c ]色烯的简明方法，使用分子间钯催化的 C - C 和分子内N-碘代琥珀酰亚胺 (NIS) 介导了关键的 C-O 键构建。
• Enantioselective Total Synthesis of (+)-Conicol via Cascade Three-Component Organocatalysis
  作者：Bor-Cherng Hong、Prakash Kotame、Chih-Wei Tsai、Ju-Hsiou Liao

  DOI：10.1021/ol902840x

  日期：2010.2.19

  The first asymmetric total synthesis of (+)-conicol has been achieved via a key step reaction involving the organocatalytic domino oxa-Michael-Michael-Michael-aldol condensation of 2-((E)-2-nitrovinyl)benzene-1,4-diol and alpha,beta-unsaturated aldehydes. Structures of the three-component domino reaction adducts, 20 and 21, including their absolute configurations, were confirmed unambiguously by X-ray analysis. Through this work, the absolute configuration of (+)-conicol was thereby elucidated.