(+)-campholenol | 36789-58-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (+)-campholenol
• 英文别名: (-)-campholenic alcohol；(-)-(1S)-2-(2,2,3-trimethylcyclopent-3-enyl)ethanol；3-Cyclopentene-1-ethanol, 2,2,3-trimethyl-, (S)-；2-[(1S)-2,2,3-trimethylcyclopent-3-en-1-yl]ethanol
• CAS: 36789-58-9
• 化学式: C₁₀H₁₈O
• 分子量: 154.252
• InChiKey: NPGPPCSBEMHHCR-VIFPVBQESA-N

物化性质

• 沸点：
  209.3±9.0 °C(Predicted)
• 密度：
  0.889±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (+)-campholenol 在 吡啶 、 4-二甲氨基吡啶 、 lithium hydroxide 、 sodium hydroxide 、 18-冠醚-6 、 二甲基硫 、 双氧水 、 氧气 、 tetraphenylporphyrin 、 乙酸酐 、 氢气 、 sodium hydride 、 potassium carbonate 、 臭氧 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二甲醚 、 二氯甲烷 、 水 、 苯 为溶剂， 生成 [(1R,3aR,6aR)-1-(2-Methoxy-ethyl)-2,2-dimethyl-5-oxo-hexahydro-pentalen-3a-yl]-acetic acid methyl ester
  参考文献：
  名称：

  Liu, Hsing-Jang; Llinas-Brunet, Montse, Canadian Journal of Chemistry, 1988, vol. 66, p. 528 - 530

  摘要：

  DOI：
• 作为产物：
  描述：

  (-)-(1S)-(2,2,3-trimethylcyclopent-3-en-1-yl)acetic acid 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 (+)-campholenol
  参考文献：
  名称：

  Liu, Hsing-Jang; Llinas-Brunet, Montse, Canadian Journal of Chemistry, 1988, vol. 66, p. 528 - 530

  摘要：

  DOI：

文献信息

• Adamantane-Monoterpenoid Conjugates Linked via Heterocyclic Linkers Enhance the Cytotoxic Effect of Topotecan
  作者：Aldar A. Munkuev、Nadezhda S. Dyrkheeva、Tatyana E. Kornienko、Ekaterina S. Ilina、Dmitry I. Ivankin、Evgeniy V. Suslov、Dina V. Korchagina、Yuriy V. Gatilov、Alexandra L. Zakharenko、Anastasia A. Malakhova、Jóhannes Reynisson、Konstantin P. Volcho、Nariman F. Salakhutdinov、Olga I. Lavrik

  DOI：10.3390/molecules27113374

  日期：——

  Inhibiting tyrosyl-DNA phosphodiesterase 1 (TDP1) is a promising strategy for increasing the effectiveness of existing antitumor therapy since it can remove the DNA lesions caused by anticancer drugs, which form covalent complexes with topoisomerase 1 (TOP1). Here, new adamantane–monoterpene conjugates with a 1,2,4-triazole or 1,3,4-thiadiazole linker core were synthesized, where (+)-and (−)-campholenic and (+)-camphor derivatives were used as monoterpene fragments. The campholenic derivatives 14a–14b and 15a–b showed activity against TDP1 at a low micromolar range with IC50 ~5–6 μM, whereas camphor-containing compounds 16 and 17 were ineffective. Surprisingly, all the compounds synthesized demonstrated a clear synergy with topotecan, a TOP1 poison, regardless of their ability to inhibit TDP1. These findings imply that different pathways of enhancing topotecan toxicity other than the inhibition of TDP1 can be realized.

  抑制酪氨酸-DNA磷酸二酯酶1（TDP1）是一种增加现有抗肿瘤治疗效果的有希望的策略，因为它可以去除由抗癌药物引起的DNA损伤，这些损伤与拓扑异构酶1（TOP1）形成共价复合物。在这里，合成了具有1,2,4-三唑或1,3,4-噻二唑连接核心的新的金刚烷-单萜共轭物，其中使用了（+）-和（-）-香叶烯和（+）-薄荷醇衍生物作为单萜片段。香叶烯衍生物14a-14b和15a-b在低微摩尔范围内对TDP1表现出活性，IC50约为5-6μM，而含薄荷醇的化合物16和17则无效。令人惊讶的是，所有合成的化合物都表现出与TOP1毒素拓扑替诺酮的明显协同作用，无论它们是否能抑制TDP1。这些发现意味着可以实现除抑制TDP1之外的不同途径来增强拓扑替诺酮的毒性。
• Monoterpene substituted thiazolidin-4-ones as novel TDP1 inhibitors: Synthesis, biological evaluation and docking
  作者：Dmitry I. Ivankin、Nadezhda S. Dyrkheeva、Alexandra L. Zakharenko、Ekaterina S. Ilina、Timofey O. Zarkov、Jóhannes Reynisson、Olga A. Luzina、Konstantin P. Volcho、Nariman F. Salakhutdinov、Olga I. Lavrik

  DOI：10.1016/j.bmcl.2022.128909

  日期：2022.10

  Tyrosyl-DNA phosphodiesterase 1(TDP1) is a promising target for a new therapy in oncological disease as an adjunct to topoisomerase 1 (TOP1) drugs. In this paper, novel thiazolidin-4-one derivatives with a benzyl and monoterpene substituents were synthesized. Compounds with a monoterpene fragment attached via a phenyloxy linker were active against TDP1 with IC50 values in the 1 ÷ 3 μM range, while

  酪氨酰-DNA 磷酸二酯酶 1 (TDP1) 作为拓扑异构酶 1 (TOP1) 药物的辅助药物，是肿瘤疾病新疗法的一个有希望的靶点。本文合成了具有苄基和单萜取代基的新型噻唑烷-4-酮衍生物。具有通过苯氧基接头连接的单萜片段的化合物对 TDP1 具有活性，IC 50值在 1 ÷ 3 μM 范围内，而单萜部分直接连接到 thiazolidin-4-one 片段没有活性。分子模型预测了活性化合物的两种可能的结合模式，都有效地阻止了对 TDP 催化位点的访问。在无毒浓度下，活性配体增强了 TOP1 毒拓扑替康在人宫颈癌 HeLa 细胞中的功效，但在非癌性 HEK293A 细胞中没有。
• Enantioselective syntheses of diquinane and (cis, anti, cis)-linear triquinanes
  作者：A. Srikrishna、Vijayendran Gowri、Ghodke Neetu

  DOI：10.1016/j.tetasy.2010.01.014

  日期：2010.2

  The enantioselective syntheses of diquinane and cis, anti, cis-linear triquinanes, starting from the readily available (S)-campholenaldehyde, employing an intramolecular rhodium carbenoid CH insertion reaction, are described. (C) 2010 Elsevier Ltd. All rights reserved.
• New monoterpene glycosides from sunflower seeds and their protective effects against H2O2-induced myocardial cell injury
  作者：Yonghe Fei、Jianping Zhao、Yanli Liu、Xiaoran Li、Qiongming Xu、Taoyun Wang、Ikhlas A. Khan、Shilin Yang

  DOI：10.1016/j.foodchem.2015.04.079

  日期：2015.11

  Three new monoterpene glycosides (1-3) and eleven known compounds (4-14) were isolated from seeds of Helianthus annuus L. (sunflower). Their structures were determined by spectroscopic and chemical methods. All the compounds were isolated from sunflower seeds for the first time. Protective effects of compounds 1-14 against H2O2-induced H9c2 cardiomyocyte injury were evaluated, and compounds 1 and 2 showed some cell-protective effects. No significant DPPH radical scavenging activity was observed for compounds 1-14.
• DERDZINSKI, KRZYSZTOF;GORA, JOZEF
  作者：DERDZINSKI, KRZYSZTOF、GORA, JOZEF

  DOI：——

  日期：——