grandinol | 63861-11-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: grandinol
• 英文别名: 2,4,6-Trihydroxy-3-methyl-5-(3-methylbutanoyl)benzaldehyde
• CAS: 63861-11-0
• 化学式: C₁₃H₁₆O₅
• 分子量: 252.267
• InChiKey: NGJANBBWZSMYRM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  94.8
• 氢给体数：
  3
• 氢受体数：
  5

安全信息

• 海关编码：
  2914400090

反应信息

• 作为反应物：
  描述：

  萜品油烯 、 grandinol 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 硝基甲烷 为溶剂， 反应 0.5h， 生成 euglobal G12
  参考文献：
  名称：

  Five phloroglucinol-monoterpene adducts from Eucalyptus grandis

  摘要：

  Five new euglobals possessing the phlorogiucinol-monoterpene structure, euglobals G8-G12, together with a known euglobal-IIc were isolated from the hexane fraction of the methanol extract of the leaves of Eucalyptus grandis. Euglobal-G8 is an adduct of formyl-isovaleroyl-phloroglucinol and gamma-terpinene whereas -G9, -G10 and -G11 have the same phloroglucinol moiety fused with alpha-terpinene, while Euglobal-G12 has terpinolene fused with the same phloroglucinol moiety. The structures of these compounds were elucidated on the basis of spectral evidences. Biomimetic synthesis of euglobals suggests that these compounds are derived biogenetically by the Diels-Alder type cycloaddition of the corresponding terpenes with an ortho-quinone methide generated from grandinol. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(98)00289-1
• 作为产物：
  描述：

  苯异戊二酮 在 氢氧化钾 、 三氯氧磷 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 grandinol
  参考文献：
  名称：

  从 Eucalyptus jensenii 中分离的 Jensenone 的高效两步合成。类似物的合成和作为抗氧化剂的评价

  摘要：

  一种从桉树叶中分离的间苯三酚衍生物 jensenone (1) 首次通过从市售间苯三酚开始的短而有效的两步程序合成。该方法提供了一种简化的途径来引入二甲酰基部分，以合成具有生物活性的甲酰化间苯三酚化合物，例如抗疟药、癌症化学预防 euglobals 和防污铁木糖醛。还合成了几种詹塞酮类似物并评估了抗氧化能力。

  DOI：

  10.1071/ch05061

文献信息

• Electrochemical synthesis of euglobal-G1, -G2, -G3, -G4, -T1 and -IIc
  作者：Kazuhiro Chiba、Takaaki Arakawa、Masahiro Tada

  DOI：10.1039/a802306i

  日期：——

  Six natural euglobals were synthesized by electrochemical methods. In a key step, cycloaddition between in situ generated quinomethanes and terpenes was performed on the surface of PTFE-fibre coated electrode to give natural products using 2,3-dichloro-5,6-dicyano-p-hydroquinone (DDQH2) as a redox mediator. In this reaction system, biomimetic generation and cycloaddition of the unstable quinomethanes were efficiently completed by the selective oxidation of cresol derivatives.

  通过电化学方法合成了六种天然尤格洛布林。关键步骤是在聚四氟乙烯纤维涂层电极表面，现场生成的喹诺甲烷与萜类化合物进行环加成反应，以2,3-二氯-5,6-二氰基对苯二酚（DDQH2）作为氧化还原介质，得到天然产物。在该反应体系中，通过对甲酚衍生物的选择性氧化，高效地完成了不稳定喹诺甲烷的仿生生成和环加成反应。
• Synthesis of euglobal-G3 and -G4
  作者：Kazuhiro Chiba、Takaaki Arakawa、Masahiro Tada

  DOI：10.1039/cc9960001763

  日期：——

  The first, concise synthesis of euglobals is accomplished by biomimetic cycloaddition of β-pinene and quinone methides generated by oxidation of grandinol.

  首个简洁的尤戈全球合成是通过生物仿制的环加成反应，使用由格兰迪烯氧化生成的β-松油烯和醌烯醇。
• Biomimetic Synthesis and Chemical Proteomics Reveal the Mechanism of Action and Functional Targets of Phloroglucinol Meroterpenoids
  作者：Amy K. Bracken、Colby E. Gekko、Nina O. Suss、Emma E. Lueders、Qi Cui、Qin Fu、Andy C. W. Lui、Elizabeth T. Anderson、Sheng Zhang、Mikail E. Abbasov

  DOI：10.1021/jacs.3c10741

  日期：2024.1.31

  biological processes governed by these modifications. Phloroglucinol meroterpenoids constitute one of the most expansive classes of natural products, displaying a plethora of biological activities. However, their mechanism of action and cellular targets have, until now, remained elusive. In this study, we detail the concise biomimetic synthesis, computational mechanistic insights, physicochemical attributes

  天然产物常年成为药物先导物和化学探针的多产来源，推动了许多治疗方法的发展。尽管它们稀缺，但通过与赖氨酸残基的共价相互作用调节蛋白质功能的天然产物具有巨大的潜力，可以解锁新的治疗干预措施，并促进我们对受这些修饰控制的生物过程的理解。间苯三酚硫萜类化合物是最广泛的天然产物类别之一，显示出大量的生物活性。然而，直到现在，它们的作用机制和细胞靶标仍然难以捉摸。在这项研究中，我们详细介绍了几种间苯三酚甲萜类化合物的简明仿生合成、计算机制、物理化学属性、动力学参数、分子作用机制和功能性细胞靶标。我们利用天然产物的合成可点击类似物，通过凝胶内荧光扫描和细胞成像来探测它们不同的蛋白质组范围反应性和亚细胞定位。通过实施样品多路复用和重新设计的赖氨酸靶向探针，我们简化了基于定量活性的蛋白质分析，从而能够直接绘制人类细胞中蛋白质赖氨酸的整体反应性和配体性。利用这个框架，我们在乳腺癌细胞中可处理的蛋白质位点确定了
• Biomimetic synthesis, antimicrobial, antileishmanial and antimalarial activities of euglobals and their analogues
  作者：Sandip B. Bharate、Kamlesh K. Bhutani、Shabana I. Khan、Babu L. Tekwani、Melissa R. Jacob、Ikhlas A. Khan、Inder Pal Singh

  DOI：10.1016/j.bmc.2005.10.027

  日期：2006.3

  In the present communication, naturally occurring phloroglucinol-monoterpene adducts, euglobals G1-G4 (3b/a and 4a/b) and 16 new analogues (13a/b-18a/b and 19-22) were synthesized by biomimetic approach. These synthetic compounds differ from natural euglobals in the nature of monoterpene and acyl functionality. All of these compounds were evaluated for their antibacterial, antifungal, antileishmanial and antimalarial activities. Analogue 17b possessed good antibacterial activity against methicillin-resistant Staphylococcus aureus, while analogues 19-22 possessed potent antifungal activity against Candida glabrata with IC(50)s ranging from 1.5 to 2.5 mu g/mL. Euglobals along with all synthesized analogues exhibited antileishmanial activity. Amongst these, euglobal G2 (3a), G3 (4a) and analogues 13a and 14a showed potent antileishmanial activity with IC50s ranging from 2.8 to 3.9 mu g/mL. Analogue 16a possessed antimalarial activity against chloroquine sensitive D6 clone of Plasmodium falciparum. None of the compounds showed toxicity against mammalian kidney fibroblasts (vero cells) upto the concentration of 4.76 mu g/ml. (c) 2005 Elsevier Ltd. All rights reserved.
• Bolte, Matthew L.; Crow, Wilfrid D.; Takahashi, Nobutaka, Agricultural and Biological Chemistry, 1985, vol. 49, # 3, p. 761 - 768
  作者：Bolte, Matthew L.、Crow, Wilfrid D.、Takahashi, Nobutaka、Sakurai, Akira、Uji-Ie, Masami、Yoshida, Shigeo

  DOI：——

  日期：——