malasseziazole C

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: malasseziazole C
• 英文别名: 12-formyl-5,11-dihydroindolo[3,2-b]carbazole-6-carboxylic acid；Malasseziazole C；6-formyl-5,11-dihydroindolo[3,2-b]carbazole-12-carboxylic acid
• 化学式: C₂₀H₁₂N₂O₃
• 分子量: 328.327
• InChiKey: ZUEZOQULQLAXBW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  86
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  diethyl 5,11-dihydroindolo[3,2-b]carbazole-6,12-dicarboxylate 在 lithium aluminium tetrahydride 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 potassium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 水 为溶剂， 反应 3.0h， 生成 malasseziazole C
  参考文献：
  名称：

  Palladium-Catalyzed Approach to Malasseziazole A and First Total Synthesis of Malasseziazole C

  摘要：

  We describe a convergent route to 5,11-dihydroindolo[3,2-b]carbazoles using a twofold oxidative cyclization as key step. The method has been applied to the synthesis of a precursor for malasseziazole A and to the first total synthesis of malasseziazole C.

  DOI：

  10.1055/s-0034-1380713

文献信息

• [1 + 2 + 3] Annulation as a General Access to Indolo[3,2-<i>b</i>]carbazoles: Synthesis of Malasseziazole C
  作者：Jinhuan Dong、Dawei Zhang、Yang Men、Xueming Zhang、Zhongyan Hu、Xianxiu Xu

  DOI：10.1021/acs.orglett.8b03646

  日期：2019.1.4

  A formal [1 + 2 + 3] annulation of methyleneindolinones with o-alkenyl arylisocyanides has been developed for the general and efficient synthesis of both symmetrical and unsymmetrical indolo[3,2-b]carbazoles. The chemoselectivity of this domino reaction was tuned by a tethered alkenyl group, which enables successive formation of three new bonds and two rings from readily accessible starting materials

  已开发了一种亚甲基吲哚酮与邻链烯基芳基异氰酸酯的正式[1 + 2 + 3]环合结构，用于对称和不对称的吲哚[3,2- b ]咔唑的常规合成。该多米诺反应的化学选择性通过束缚链烯基进行调节，该链烯基能够在一次操作中由易于接近的起始原料连续形成三个新键和两个环。此外，该方法被用作生物碱麦拉西唑C合成中的关键步骤。
• Photoprotective compositions containing malassezia-derived compounds and/or chemical analogs thereof
  申请人：Versicolor Technologies, LLC

  公开号：US11202748B2

  公开（公告）日：2021-12-21

  The present invention relates to compounds, compositions, and methods for modulating skin pigmentation and treating or preventing UV-induced skin damage, erythema, aging of the skin, sunburn, and hyperpigmentation in a subject. The compounds, compositions, and methods of the present invention generally involve Malassezia-derived compounds, including malassezin and indirubin, and/or chemical analogs thereof. Other applications of the compounds and compositions disclosed herein include, but are not limited to, improving hyperpigmentation caused by a hyperpigmentation disorder, inducing melanocyte apoptosis, and modulating arylhydrocarbon receptor (AhR) activity, melanogenesis, melanin production, melanosome biogenesis, melanosome transfer, melanocyte activity, and melanin concentration.

  本发明涉及调节皮肤色素沉着和治疗或预防紫外线引起的皮肤损伤、红斑、皮肤老化、晒伤和受试者色素沉着的化合物、组合物和方法。本发明的化合物、组合物和方法通常涉及马拉色菌衍生的化合物，包括马拉色素和靛玉红，和/或其化学类似物。本文公开的化合物和组合物的其他应用包括但不限于改善色素沉着症引起的色素沉着，诱导黑色素细胞凋亡，调节芳基烃受体（AhR）活性、黑色素生成、黑色素生成、黑色素小体生物生成、黑色素小体转移、黑色素细胞活性和黑色素浓度。
• Palladium-Catalyzed Approach to Malasseziazole A and First Total Synthesis of Malasseziazole C
  作者：Hans-Joachim Knölker、Ute Kober

  DOI：10.1055/s-0034-1380713

  日期：——

  We describe a convergent route to 5,11-dihydroindolo[3,2-b]carbazoles using a twofold oxidative cyclization as key step. The method has been applied to the synthesis of a precursor for malasseziazole A and to the first total synthesis of malasseziazole C.