Malassezin | 352712-51-7

• 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: Malassezin
• 英文别名: 2-((1H-indol-3-yl)methyl)-1H-indole-3-carbaldehyde；CV-8684；2-(1H-indol-3-ylmethyl)-1H-indole-3-carbaldehyde
• CAS: 352712-51-7
• 化学式: C₁₈H₁₄N₂O
• 分子量: 274.322
• InChiKey: GBEJDLJINBVBFG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  48.6
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  Malassezin 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 以78%的产率得到吲哚并[3,2-b]咔唑
  参考文献：
  名称：

  WO2019200232A5

  摘要：

  公开号：

  WO2019200232A5
• 作为产物：
  描述：

  3-甲酰基吲哚酸-1-羧酸 t-丁基酯 在 叔丁基锂 、 sodium 、 三氯氧磷 作用下， 以 四氢呋喃 、 氨 、 正戊烷 为溶剂， 反应 0.75h， 生成 Malassezin
  参考文献：
  名称：

  Malassezin—a novel agonist of the Arylhydrocarbon receptor from the yeast Malassezia furfur

  摘要：

  The yeast Malassezia furfur converts tryptophan into several indole compounds. One of three malassezin, was identified as 2-( 1H-indol-3-ylmethl)- 1 H-indole-3-carbaldehyde (I). It was synthesized from N-Boc-indole-3-carbaldehyde in five steps with 12% overall yield. The compound easily cyclizes to indolo[3.2-b]carbazole (7) which is known to interact with the arylhydrocarbon receptor (AHR). Similarly, malassezin was found to induce cytochrome P450 as an agonist of AHR(EC50 = 1.57 muM) in rat hepatocytes. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00319-9

文献信息

• SYNTHESIS OF DIINDOLYLMETHANES AND INDOLO[3,2-B]CARBAZOLES, COMPOUNDS FORMED THEREBY, AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
  申请人：Wisconsin Alumni Research Foundation

  公开号：US20160039754A1

  公开（公告）日：2016-02-11

  Described is a method to make diindolylmethanes and indolyl/pyrrolylmethanes, The method includes the steps of contacting an ether comprising an arylpropargyl moiety and an amine-protected, substituted or unsubstituted aniline moiety with a substituted or unsubstituted indol or a substituted or unsubstituted pyrrole, in the presence of a metal-containing catalyst, for a time and at a temperature to cause an annulation/arylation cascade reaction that yields a diindolylmethane or a indolyl/pyrrolylmethane. The resulting compounds are effective to modulate activity of arylhydrocarbon receptors, to inhibit activity of PCSK9, and to stimulate secretion of glucagon-like peptide 1 in mammals.

  描述了一种制备二吲哚基甲烷和吲哚基/吡咯基甲烷的方法。该方法包括以下步骤：在金属催化剂的存在下，使包含芳基炔丙基部分和胺保护的、取代的或未取代的苯胺部分的醚与取代的或未取代的吲哚或取代的或未取代的吡咯接触，接触一段时间和温度，以引发环化/芳基化级联反应，从而产生二吲哚基甲烷或吲哚基/吡咯基甲烷。所得化合物能有效调节芳基烃受体的活性，抑制PCSK9的活性，并刺激哺乳动物胰高血糖素样肽1的分泌。
• ARYL HYDROCARBON RECEPTOR MODULATOR
  申请人：Ariagen, Inc.

  公开号：US20190307731A1

  公开（公告）日：2019-10-10

  Disclosed is an aryl hydrocarbon receptor modulator of formula (I), and a pharmaceutically acceptable salt thereof, wherein R′ is H, CN, CH 2 (OH)R 0 , C m H 2m+1 , C n H 2n-1 , C n H 2n-3 , two R a are independently H or two R a together form ═O or ═N—W 3 —R 1 ; A is a C 6 to C 10 aromatic ring unsubstituted or substituted with 1 to 3 R, or a C 2 -C 10 heteroaromatic ring interrupted by 1 to 5 heteroatoms selected from N, O, and S or a 4 to 7 membered nonaromatic heterocyclic ring containing C═N and interrupted by 1 to 3 heteroatoms selected from N, O, and S, with either one unsubstituted or substituted with 1 to 3 R; Q is R, or is a C 6 to C 10 aromatic ring or a C 2 to C 10 heteroaromatic ring unsubstituted or substituted with 1 to 3 R and interrupted by 1 to 5 heteroatoms selected from N, O, and S; and R is R c which is C-attached or R N which is N-attached. The compounds of formula (I) of the present invention can regulate AhR activity, and can be used to inhibit the growth of cancer cells and inhibit the metastasis and invasion of tumor cells.

  本发明揭示了一种化学式（I）的芳香烃受体调节剂及其药用可接受盐，其中R′为H、CN、CH2（OH）R0、CmH2m+1、CnH2n-1、CnH2n-3，两个Ra独立地为H或两个Ra共同形成═O或═N—W3—R1；A为未取代或取代1至3个R的C6至C10芳香环，或由N、O和S中选择的1至5个杂原子中断的C2-C10杂芳环，或含有C═N并由N、O和S中选择的1至3个杂原子中断的4至7个成员的非芳杂环，其中一个未取代或取代1至3个R；Q为R，或者是未取代或取代1至3个R并由N、O和S中断的C6至C10芳香环或C2至C10杂芳环；R为C-连接的Rc或N-连接的RN。本发明的化合物可以调节AhR活性，可用于抑制癌细胞的生长，以及抑制肿瘤细胞的转移和侵袭。
• MALASSEZIN AND ANALOGS THEREOF AS SKIN BRIGHTENING AGENTS
  申请人：Einziger Michael

  公开号：US20170260133A1

  公开（公告）日：2017-09-14

  The present invention relates to compounds, compositions, and methods for brightening skin. The compounds, compositions, and methods of the present invention generally involve compounds produced by a Malassezia yeast, and chemical analogs thereof. In addition to skin brightening applications, the compounds, compositions, and methods of the present invention may be used to modulate melanocyte activity, induce melanocyte apoptosis, agonize an arylhydrocarbon receptor (AhR), improve hyperpigmentation caused by a hyperpigmentation disorder, and modulate melanin production, melanosome biogenesis, and melanosome transfer.

  本发明涉及用于美白皮肤的化合物、组合物和方法。本发明的化合物、组合物和方法通常涉及由Malassezia酵母产生的化合物及其化学类似物。除了用于美白皮肤的应用外，本发明的化合物、组合物和方法还可用于调节黑色素细胞活性、诱导黑色素细胞凋亡、激活芳烃受体（AhR）、改善由于色素沉着紊乱引起的色素沉着过度，并调节黑色素生成、黑色素体生物合成和黑色素体转移。
• PHOTOPROTECTIVE COMPOSITIONS CONTAINING MALASSEZIA-DERIVED COMPOUNDS AND/OR CHEMICAL ANALOGS THEREOF
  申请人：Einziger, Michael

  公开号：EP3957639A1

  公开（公告）日：2022-02-23

  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。
• Malassezin and analogs thereof as skin brightening agents
  申请人：Einziger Michael

  公开号：US10131631B2

  公开（公告）日：2018-11-20

  The present invention relates to compounds, compositions, and methods for brightening skin. The compounds, compositions, and methods of the present invention generally involve compounds produced by a Malassezia yeast, and chemical analogs thereof. In addition to skin brightening applications, the compounds, compositions, and methods of the present invention may be used to modulate melanocyte activity, induce melanocyte apoptosis, agonize an arylhydrocarbon receptor (AhR), improve hyperpigmentation caused by a hyperpigmentation disorder, and modulate melanin production, melanosome biogenesis, and melanosome transfer.

  本发明涉及美白皮肤的化合物、组合物和方法。本发明的化合物、组合物和方法一般涉及马拉色菌酵母产生的化合物及其化学类似物。除皮肤增白应用外，本发明的化合物、组合物和方法还可用于调节黑色素细胞活性、诱导黑色素细胞凋亡、激动芳基烃受体（AhR）、改善色素沉着症引起的色素沉着，以及调节黑色素生成、黑色素小体生物生成和黑色素小体转移。