5-异丙基-3,8-二甲基-2-萘酚 | 2102-75-2

• 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
• 中文名称: 5-异丙基-3,8-二甲基-2-萘酚
• 英文名称: 7-hydroxycadalene
• 英文别名: 3,8-dimethyl-5-propan-2-ylnaphthalen-2-ol
• CAS: 2102-75-2
• 化学式: C₁₅H₁₈O
• mdl: MFCD24392778
• 分子量: 214.307
• InChiKey: RIWNMJBJRPCUBX-UHFFFAOYSA-N

物化性质

• 保留指数：
  1986

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  5-异丙基-3,8-二甲基-2-萘酚 在 氧气 作用下， 以 氯仿 为溶剂， 反应 240.0h， 以35%的产率得到3,8-二甲基-5-异丙基-1,2-萘醌
  参考文献：
  名称：

  Formation of the ortho-quinone mansonone C from 7-hydroxycadalene on silica gel

  摘要：

  DOI：

  10.1016/s0031-9422(00)98110-x
• 作为产物：
  描述：

  5-异丙基-2-甲基-2-环己烯-1-酮 在 palladium on activated charcoal 、 二苯醚 、 乙醇 、 吗啡啉盐酸盐 作用下， 生成 5-异丙基-3,8-二甲基-2-萘酚
  参考文献：
  名称：

  Briggs et al., Journal of the Chemical Society, 1949, p. 1098,1100

  摘要：

  DOI：

文献信息

• Synthesis of hydroxycadalene and hydroxycalamenene via 13-hydroxyxanthorrhizol, a possible precursor of parvifolin
  作者：Wolfgang Krause、Ferdinand Bohlmann

  DOI：10.1016/s0040-4039(00)96151-3

  日期：1987.1

  Starting with an acetophenone derivative three sesquiterpenes, xanthorrhizol, hydroxycadalene and hydroxycalamenene were synthesized. The biomimetic formation of parvifolin could not be achieved.

  从苯乙酮衍生物开始，合成了三个倍半萜烯，黄嘌呤酚，羟基cadalene和羟基cal烯。parvifolin的仿生形成无法实现。
• Antimicrobial Agents from<i>Heterotheca inuloides</i>
  作者：Isao Kubo、Hisae Muroi、Aya Kubo、Swapan Chaudhuri、Yolanda Sanchez、Tetsuya Ogura

  DOI：10.1055/s-2006-959462

  日期：1994.6

  By bioassay directed fractionation, four sesquiterpenoids 1 - 4 were isolated as antimicrobial agents from the dried flowers of Heterotheca inuloides, a Mexican medicinal plant locally known as “arnica”. 7-Hydroxy-3,4-dihydrocadalin (3) and 7-hydroxycadalin (4) exhibited potent antibacterial activity against Gram-positive bacteria with minimum inhibitory concentrations (MICs) ranging from 6.25 to 12.5 µg/ml. Notably, 7-hydroxy-3,4-dihydrocadalin showed bactericidal activity against methicillin-resistant Staphylococcus aureus (MRSA) with a minimum bactericidal concentration (MBC) of 12.5 µg/ml.

  通过生物测定定向分馏，从 Heterotheca inuloides（一种墨西哥药用植物，当地称为 "山金车"）的干燥花中分离出四种倍半萜 1 - 4，作为抗菌剂。7-Hydroxy-3,4-dihydrocadalin (3) 和 7-hydroxycadalin (4) 对革兰氏阳性细菌具有很强的抗菌活性，最低抑菌浓度为 6.25 至 12.5 µg/ml。值得注意的是，7-羟基-3,4-二氢蟾蜍甙对耐甲氧西林金黄色葡萄球菌（MRSA）具有杀菌活性，最低杀菌浓度（MBC）为 12.5 µg/ml。
• Studies in terpenoids—XVII
  作者：Jose Alexander、G.S.Krishna Rao

  DOI：10.1016/s0040-4020(01)90732-x

  日期：1971.1

  The synthesis and facile elaboration of 7-methoxycalamenal (4b) to four naturally occurring phenolic sesquiterpenoids, 7-hydroxycalamenene (4e), 7-hydroxycadalene (13e), 7-hydroxycalamenal (4f), and 7-hydroxycadalenal (13f) are described.

  描述了将7-甲氧基金刚烷醛（4b）合成为四种天然存在的酚倍半萜类化合物，7-羟基a金烯（4e），7-羟基cadalene（13e），7-羟基金刚烷醛（4f）和7-羟基金刚烷醛（13f）并对其进行了简单的修饰。
• Toxicological evaluation of the natural products and some semisynthetic derivatives of Heterotheca inuloides Cass (Asteraceae)
  作者：José Luis Rodríguez-Chávez、Elvia Coballase-Urrutia、Gloria Sicilia-Argumedo、Teresa Ramírez-Apan、Guillermo Delgado

  DOI：10.1016/j.jep.2015.08.055

  日期：2015.12

  quercetin-3,7,3'-trimethyl ether (7), quercetin-3,7,3',4'-tetramethyl ether (8), eriodictyol-7,4'-dimethyl ether (9), α-spinasterol (10), caryolan-1,9β-diol (11) and 7-(3,3-dimethylallyloxy)-coumarin (12) as well as the toxic aspects of the semisynthetic compounds 7-acetoxy-3,4-dihydrocadalene (13), 7-benzoxy-3,4-dihydrocadalene (14), 7-acetoxycadalene (15), 7-benzoxycadalene (16), quercetin pentaacetate (17)

  族裔药理关系Heterotheca ineuloides Cass（Asteraceae），广为人称的墨西哥蜜rn（árnicamexicana），在墨西哥传统医学中广泛用于治疗瘀伤，皮肤病，风湿性疼痛以及其他癌症疾病。inuloides中的主要成分是卡丹烷型倍半萜，类黄酮和植物甾醇。已证明具有卡丁烷骨架的化合物对人肿瘤细胞系和盐水虾具有细胞毒活性，并在不同的动物物种中显示出毒性作用。尽管这种植物已经被广泛使用，但是关于安全性和毒性，特别是纯化合物的安全性和毒性很少有可用信息。这项研究的目的是评估从麻黄和一些半合成衍生物中分离出来的天然产物的潜在毒性。6-二甲基苯并[c]氧杂环丁烷-7,9-二酮（20）。通过磺基罗丹明B（SRB）测定，卤虫盐碱测定，RAW264.7巨噬细胞测定化合物的毒性。此外，还评估了化合物1（从丙酮提取物中分离出的主要天然倍半萜烯）对小鼠的急性毒性。结果观察到最佳结果
• Effect of natural and semi-synthetic cadinanes from Heterotheca inuloides on NF-κB, Nrf2 and STAT3 signaling pathways and evaluation of their in vitro cytotoxicity in human cancer cell lines
  作者：Verónica Egas、Estrella Millán、Juan A. Collado、Teresa Ramírez-Apan、Carlos A. Méndez-Cuesta、Eduardo Muñoz、Guillermo Delgado

  DOI：10.1016/j.bmc.2017.03.069

  日期：2017.6

  The effects of ten natural cadinane sesquiterpenoids isolated from Heterotheca inuloides on the pathways of the NF-kappa B, Nrf2 and STAT3 transcription factors were studied for the first time. The main constituent in this species, 7-hydroxy-3,4-dihydrocadalene (1), showed anti-NE-kappa B activity and activated the antioxidant Nrf2 pathway, which may explain the properties reported for the traditional use of the plant. In addition to the main metabolite, a structurally similar compound, 7-hydroxy-cadalene (2), also displayed anti-NE-kappa B activity. Thus, both natural compounds were used as templates for the preparation of a novel semi-synthetic derivative set, including esters and carbamates, which were evaluated for their potential in vitro antiproliferative activities against six human cancer cell lines. Carbamate derivatives 32 and 33 were found to exhibit potent activity against human colorectal adenocarcinoma and showed important selectivity in cancer cells. Among ester derivatives, compound 13 was determined to be a more potent NE-kappa B inhibitor and Nrf2 activator than its parent, 7-hydroxy-3,4-dihydrocadalene (1). Furthermore, this compound decreases levels of phospho-IKBa, a protein complex involved in the NE-kappa B activation pathway. Molecular simulations suggest that all active compounds interact with the activation loop of the IKKI3 subunit in the IKK complex, which is the responsible of IKBoc phosphorylation. Thus, we identified two natural, and one semi-synthetic, NF-kappa B and Nrf2 modulators and two new promising cytotoxic compounds. (C) 2017 Elsevier Ltd. All rights reserved.