2-[2-(Hydroxymethyl)-6-(methoxymethoxy)-4-methylphenyl]-5-(methoxymethoxy)naphthalene-1,4-dione | 1354710-43-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-[2-(Hydroxymethyl)-6-(methoxymethoxy)-4-methylphenyl]-5-(methoxymethoxy)naphthalene-1,4-dione
• CAS: 1354710-43-2
• 化学式: C₂₂H₂₂O₇
• 分子量: 398.412
• InChiKey: WOPKBAXQUIOYFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  91.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-[2-(Hydroxymethyl)-6-(methoxymethoxy)-4-methylphenyl]-5-(methoxymethoxy)naphthalene-1,4-dione 在 戴斯-马丁氧化剂 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 8.5h， 生成
  参考文献：
  名称：

  Synthesis of jadomycin A and related jadomycin aglycons: structural re-examination of jadomycins S and T may be needed

  摘要：

  Jadomycin A and related jadomycin M and W aglycons were synthesized. Easy re-construction of 4(hydroxymethyl)-1,3-oxazolidin-5-one system into an isomeric 1,3-oxazolidine-4-carboxylic acid system during the synthetic trial of jadomycin S aglycon requests us to more precisely re-examine the structures proposed for jadomycins S and T, derived from hydroxyl-containing amino acids of L-serine and L-threonine, respectively. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.10.160
• 作为产物：
  描述：

  [3-(methoxymethoxy)-5-methylphenyl]methanol 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 正丁基锂 、 cesium fluoride 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 水 为溶剂， 反应 45.5h， 生成 2-[2-(Hydroxymethyl)-6-(methoxymethoxy)-4-methylphenyl]-5-(methoxymethoxy)naphthalene-1,4-dione
  参考文献：
  名称：

  Synthesis of jadomycin A and related jadomycin aglycons: structural re-examination of jadomycins S and T may be needed

  摘要：

  Jadomycin A and related jadomycin M and W aglycons were synthesized. Easy re-construction of 4(hydroxymethyl)-1,3-oxazolidin-5-one system into an isomeric 1,3-oxazolidine-4-carboxylic acid system during the synthetic trial of jadomycin S aglycon requests us to more precisely re-examine the structures proposed for jadomycins S and T, derived from hydroxyl-containing amino acids of L-serine and L-threonine, respectively. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.10.160

文献信息

• Synthesis and <i>in Vitro</i> Cytotoxicity Evaluation of Jadomycins
  作者：Erika Iwasaki、Yoshimi Shimizu、Yusuke Akagi、Toshiya Komatsu

  DOI：10.1248/cpb.c23-00351

  日期：2023.9.1

  ISP5230, exhibit cytotoxic activity against multidrug-resistant breast cancer cells. We have previously achieved the total synthesis of jadomycins using the direct arylation of juglone as a key step. In this study, we achieved the total synthesis of jadomycin T and jadomycin aglycons using L-threonine and 1-amino-2-propanol as nitrogen sources. Additionally, we evaluated the cytotoxic activity of eight

  Jadomycins 是从委内瑞拉链霉菌ISP5230 中分离出来的苯并[ b ]菲啶型生物碱，对多重耐药乳腺癌细胞具有细胞毒活性。我们之前以胡桃醌的直接芳基化为关键步骤，实现了贾多霉素的全合成。本研究以L-苏氨酸和1-氨基-2-丙醇为氮源，实现了贾多霉素T和贾多霉素苷元的全合成。此外，我们还评估了 8 种化合物（包括糖苷、jadomycin T 及其相应的苷元）在 8 种肿瘤细胞中的细胞毒活性。所评估的贾多霉素作为苷元往往表现出比作为糖苷更强的细胞毒活性。虽然源自氨基酸的1，3-恶唑烷环的存在不是必需的，但是当该环具有羧基时，1，3-恶唑烷环的存在显示出强活性。此外，与酚羟基不同位置的非天然异构体相比，天然存在的菲绿苷苷元表现出更强的细胞毒活性。此外，这项研究表明贾多霉素可能成为治疗脑肿瘤的先导化合物；然而，还需要进一步研究它们穿透血脑屏障的能力。 全尺寸图像
• Synthesis of jadomycin A and related jadomycin aglycons: structural re-examination of jadomycins S and T may be needed
  作者：Takayoshi Tajima、Yuhsuke Akagi、Takuya Kumamoto、Noriyuki Suzuki、Tsutomu Ishikawa

  DOI：10.1016/j.tetlet.2011.10.160

  日期：2012.1

  Jadomycin A and related jadomycin M and W aglycons were synthesized. Easy re-construction of 4(hydroxymethyl)-1,3-oxazolidin-5-one system into an isomeric 1,3-oxazolidine-4-carboxylic acid system during the synthetic trial of jadomycin S aglycon requests us to more precisely re-examine the structures proposed for jadomycins S and T, derived from hydroxyl-containing amino acids of L-serine and L-threonine, respectively. (C) 2011 Elsevier Ltd. All rights reserved.