2-(1H-indole-3-carbonyl)-1H-indole-3-carbaldehyde | 444574-83-8

• 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: 2-(1H-indole-3-carbonyl)-1H-indole-3-carbaldehyde
• CAS: 444574-83-8
• 化学式: C₁₈H₁₂N₂O₂
• 分子量: 288.305
• InChiKey: ZQKSRAOJBBWVCN-UHFFFAOYSA-N

物化性质

• 沸点：
  642.5±45.0 °C(Predicted)
• 密度：
  1.412±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  65.7
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(1H-indole-3-carbonyl)-1H-indole-3-carbaldehyde 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以58%的产率得到5H,11H-indolo[3,2-b]carbazole-6,12-dione
  参考文献：
  名称：

  吲哚并咔唑醌的合成；强大的芳烃受体配体

  摘要：

  描述了吲哚[2,3 - b ]咔唑-6,12-二酮和异构吲哚[3,2 - b ]咔唑-6,12-二酮的合成，这是芳烃（Ah）受体的极有效诱导剂。母体吲哚[3，2- b ]咔唑的初始氧化，然后采用几种不同的闭环策略产生了后者。还描述了不对称的6，12-二取代的吲哚[2，3- b ]咔唑的合成条目。

  DOI：

  10.1016/s0040-4020(02)00006-6
• 作为产物：
  描述：

  3-甲酰基吲哚酸-1-羧酸 t-丁基酯 在 potassium phosphate 、 四丁基氟化铵 、 叔丁基锂 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 二甲基亚砜 、 1,2-二氯乙烷 为溶剂， 反应 21.0h， 生成 2-(1H-indole-3-carbonyl)-1H-indole-3-carbaldehyde
  参考文献：
  名称：

  WO2019200232A5

  摘要：

  公开号：

  WO2019200232A5

文献信息

• 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。
• Photoprotective compositions containing Malassezia-derived compounds and/or chemical analogs thereof
  申请人：Versicolor Technologies, LLC

  公开号：US11220491B2

  公开（公告）日：2022-01-11

  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。
• PHOTOPROTECTIVE COMPOSITIONS CONTAINING MALASSEZIA-DERIVED COMPOUNDS AND/OR CHEMICAL ANALOGS THEREOF
  申请人：Einziger Michael

  公开号：US20190337927A1

  公开（公告）日：2019-11-07

  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 aylhydrocarbon receptor (AhR) activity, melanogenesis, melanin production, melanosome biogenesis, melanosome transfer, melanocyte activity, and melanin concentration.
• [EN] PHOTOPROTECTIVE COMPOSITIONS CONTAINING MALASSEZIA-DERIVED COMPOUNDS AND/OR CHEMICAL ANALOGS THEREOF<br/>[FR] COMPOSITIONS DE PHOTOPROTECTION CONTENANT DES COMPOSÉS DÉRIVÉS DE MALASSEZIA ET/OU DES ANALOGUES CHIMIQUES DE CEUX-CI
  申请人：EINZIGER MICHAEL

  公开号：WO2019217387A1

  公开（公告）日：2019-11-14

  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.
• [EN] PHOTOPROTECTIVE COMPOSITIONS CONTAINING MALASSEZIA-DERIVED COMPOUNDS AND/OR CHEMICAL ANALOGS THEREOF<br/>[FR] COMPOSITIONS PHOTOPROTECTRICES CONTENANT DES COMPOSÉS DÉRIVÉS DE MALASSEZIA ET/OU DES ANALOGUES CHIMIQUES DE CEUX-CI
  申请人：EINZIGER MICHAEL

  公开号：WO2019200232A1

  公开（公告）日：2019-10-17

  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.