5,6-二羟基-2-吲哚甲酸 | 4790-08-3

• 物质功能分类: 医药中间体 - 杂环化合物 - 吲哚类化合物
• 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
• 中文名称: 5,6-二羟基-2-吲哚甲酸
• 中文别名: 5,6-二羟基-1H-吲哚-2-羧酸
• 英文名称: 5,6-dihydroxy-2-carboxyindole
• 英文别名: 5,6-dihydroxyindole-2-carboxylic acid；5,6-dihydroxy-1H-indole-2-carboxylic acid；5,6-dihydroxy-2-indolylcarboxylic acid；5,6-dihydroxyindolecarboxylic acid；5,6-dihydroxy-2-carboxy indole；DHICA
• CAS: 4790-08-3
• 化学式: C₉H₇NO₄
• 分子量: 193.159
• InChiKey: YFTGOBNOJKXZJC-UHFFFAOYSA-N

物化性质

• 熔点：
  234 °C (decomp)
• 沸点：
  578.6±45.0 °C(Predicted)
• 密度：
  1.736±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  93.6
• 氢给体数：
  4
• 氢受体数：
  4

安全信息

• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335
• 储存条件：
  存储条件：2-8°C，干燥密封。

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  5-羟基-6-甲氧基-1H-吲哚-2-羧酸	5-hydroxy-6-methoxyindole-2-carboxylic acid	2495-80-9	C10H9NO4	207.186
  5,6-二甲氧基吲哚-2-甲酸	5,6-dimethoxyindole-2-carboxylic acid	88210-96-2	C11H11NO4	221.213
  ——	methyl 5-hydroxy-6-methoxy-1H-indole-2-carboxylate	4305-32-2	C11H11NO4	221.213
  5,6-亚甲基二氧吲哚-3-羧酸	5,6-methylenedioxyindolyl-2-carboxylic acid	106517-64-0	C10H7NO4	205.17
  5,6-二甲氧基吲哚-2-羧酸甲酯	methyl 5,6-dimethoxy-1H-indole-2-carboxylate	28059-24-7	C12H13NO4	235.24
  5,6-二甲氧基吲哚-2-甲酸乙酯	5,6-dimethoxy-1H-indole-2-carboxylic acid ethyl ester	16382-18-6	C13H15NO4	249.266
  5H-[1,3]1,3-二氧杂环戊基[4,5-F]吲哚-6-甲酸甲酯	5H-[1,3]dioxolo[4,5-f]indole-6-carboxylic acid methyl ester	136818-52-5	C11H9NO4	219.197

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	5,6-Dihydroxy-indol-2-carbonsaeure-methylester	10131-14-3	C10H9NO4	207.186
  ——	2-ethoxycarbonyl-5,6-dihydroxyindole	113370-04-0	C11H11NO4	221.213
  ——	2,2'-dicarboxy-5,5',6,6'-tetrahydroxy-4,4'-biindolyl	133991-54-5	C18H12N2O8	384.302
  5,6-二羟基吲哚	1H-indole-5,6-diol	3131-52-0	C8H7NO2	149.149
  ——	1,1,1,3,3,3-Hexafluoroisopropyl 5,6-dihydroxyindole 2-carboxylate bis(pentafluoroproprionate) (ester	——	C18H5F16NO6	635.2

反应信息

• 作为反应物：
  描述：

  5,6-二羟基-2-吲哚甲酸 在 Tris buffer 、 氧气 、 copper(II) sulfate 作用下， 反应 0.17h， 以95%的产率得到2,2'-dicarboxy-5,5',6,6'-tetrahydroxy-4,4'-biindolyl
  参考文献：
  名称：

  Synthesis of optically active tetrameric melanin intermediates by oxidation of the melanogenic precursor 5,6-dihydroxyindole-2-carboxylic acid under biomimetic conditions

  摘要：

  In a recent work addressing the structural characterization of melanin pigments, we reported the isolation and characterization of trimeric oligomers of 5,6-dihydroxyindole-2-carboxylic acid (DHICA), a key intermediate in the biosynthesis of the dark brown eumelanins, by tyrosine catalyzed oxidation of the indole under biomimetic conditions. These oligomers feature atropisomerism and consequently, we wished to investigate chirality in such systems. Herein, we report two significant steps forward in this study: The isolation of a regiosymmetric DHICA tetramer by means of a model approach involving oxidation of the main DHICA dimer, namely 4,4'-biindolyl and the first resolution of eumelanin intermediates. This also allowed the absolute stereochemistry of the newly isolated tetramer to be defined by applying the exiton chirality method. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00156-3
• 作为产物：
  描述：

  左旋多巴 在 碳酸氢钠 、 potassium hexacyanoferrate(III) 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 0.33h， 以72%的产率得到5,6-二羟基-2-吲哚甲酸
  参考文献：
  名称：

  CycloDOPA及其衍生物的pH稳定性和抗氧化能力。

  摘要：

  CycloDOPA（白斑多色）是一种众所周知的酪氨酸代谢产物，它是哺乳动物有机体中黑色素的前体，也是植物中β-甘油的前体。然而，尚未广泛报道从自然来源分离出cycloDOPA。在目前的工作中，研究了在各种pH水平下cycloDOPA和cycloDOPA甲酯的稳定性。两种化合物在酸性条件下均稳定。相反，当pH值从中性变为碱性以形成吲哚衍生物作为主要产物时，两种化合物均不稳定。基于pH稳定性，首次对cycloDOPA及其衍生物进行了DPPH自由基清除测定。

  DOI：

  10.3390/molecules23081943

文献信息

• CLEAVABLE CONJUGATES OF TLR7/8 AGONIST COMPOUNDS, METHODS FOR PREPARATION, AND USES THEREOF
  申请人：Dynavax Technologies Corporation

  公开号：US20190151462A1

  公开（公告）日：2019-05-23

  The present disclosure relates to cleavable conjugates (for example, particle-based or antibody-based conjugates) of TLR7/8 agonists (for example, 1H-imidazo[4,5-c]quinoline derivatives) containing a conjugation linker, a cleavable linker, and a self-eliminating linker. The present disclosure also related to methods for preparation of the cleavable conjugates, uses thereof for stimulating an effective immune response, and uses thereof for the treatment of cancer.

  本公开涉及可切割的结合物（例如，基于颗粒或抗体的结合物），其中包含TLR7/8激动剂（例如，1H-咪唑[4,5-c]喹啉衍生物），包括结合连接物、可切割连接物和自消除连接物。本公开还涉及制备可切割结合物的方法，以及将其用于刺激有效的免疫反应和用于癌症治疗的用途。
• NOVEL BINDER-DRUG CONJUGATES (ADCs) AND USE OF SAME
  申请人：SEATTLE GENETICS, INC.

  公开号：US20150246136A1

  公开（公告）日：2015-09-03

  The present patent application relates to novel binder-drug conjugates (ADCs) of N,N-dialkylauristatins directed against the target epidermal growth factor receptor (EGFR, gene ID 1956), effective metabolites of these ADCs, methods for producing these ADCs, use of these ADCs for treatment and or prevention of diseases as well as the use of these ADCs to produce pharmaceutical drugs for treatment and/or prevention of diseases, in particular hyperproliferative and/or angiogenic diseases such as cancer, for example. Such treatments may be administered as monotherapy or in combination with other pharmaceutical drugs or other therapeutic measures.

  本专利申请涉及针对靶向表皮生长因子受体（EGFR，基因ID 1956）的新型结合物-药物共轭物（ADCs）N，N-二烷基月桂酰基蛋白酶抑制剂，这些ADCs的有效代谢物，生产这些ADCs的方法，利用这些ADCs治疗和/或预防疾病，以及利用这些ADCs生产用于治疗和/或预防疾病的药物，特别是治疗高增殖和/或血管生成性疾病，如癌症。这种治疗可以作为单药疗法或与其他药物或其他治疗措施联合使用。
• Novel Binder-Drug Conjugates (ADCs) and Use of Same
  申请人：Lerchen Hans-Georg

  公开号：US20140127240A1

  公开（公告）日：2014-05-08

  The present patent application relates to novel binder-drug conjugates (ADCs) of N,N-dialkylauristatins directed against the target epidermal growth factor receptor (EGFR, gene ID 1956), effective metabolites of these ADCs, methods for producing these ADCs, use of these ADCs for treatment and or prevention of diseases as well as the use of these ADCs to produce pharmaceutical drugs for treatment and/or prevention of diseases, in particular hyperproliferative and/or angiogenic diseases such as cancer, for example. Such treatments may be administered as monotherapy or in combination with other pharmaceutical drugs or other therapeutic measures.

  本专利申请涉及针对表皮生长因子受体（EGFR，基因ID 1956）的新型结合物-药物共轭物（ADCs）N，N-二烷基月桂酰基蛋白酶抑制剂，这些ADCs的有效代谢物，生产这些ADCs的方法，利用这些ADCs治疗和/或预防疾病以及利用这些ADCs生产用于治疗和/或预防疾病的药物，特别是治疗高增殖和/或血管生成性疾病，如癌症。这种治疗可以作为单药疗法或与其他药物或其他治疗措施联合使用。
• NOVEL COMPOUND HAVING SKIN-WHITENING, ANTI-OXIDIZING AND PPAR ACTIVITIES AND MEDICAL USE THEREFOR
  申请人：Chung Hae Young

  公开号：US20140037564A1

  公开（公告）日：2014-02-06

  Provided are a novel compound having skin-whitening, anti-oxidizing and PPAR activities and a medical use thereof, and the compound has skin-whitening activities for the suppression of tyrosinase, and accordingly, is useful for use in skin-whitening pharmaceutical composition or cosmetic products; has anti-oxidant activities, and accordingly, is useful for the prevention and treatment of skin-aging; and has PPAR activities, and in particular, PPARα and PPARγ activities, and accordingly, is useful for use in pharmaceutical compositions or health foods which are effective for the prevention and treatment of obesity, metabolic disease, or cardiovascular disease.

  提供了一种具有美白皮肤、抗氧化和PPAR活性的新化合物及其医药用途，该化合物具有抑制酪氨酸酶的美白皮肤活性，因此适用于用于美白皮肤的药用组合物或化妆品；具有抗氧化活性，因此适用于预防和治疗皮肤衰老；具有PPAR活性，特别是PPARα和PPARγ活性，因此适用于用于预防和治疗肥胖、代谢性疾病或心血管疾病的药用组合物或保健食品。
• HAIR DYE AGENT COMPRISING AMINOPYRIMIDINE DERIVATIVES
  申请人：Henkel AG & Co. KGaA

  公开号：US20150209258A1

  公开（公告）日：2015-07-30

  The present application relates to agents for dyeing keratin fibers, in particular human hair, the agent including a cosmetic carrier and at least a compound of formula (I)

  本申请涉及染色角蛋白纤维的药剂，特别是人类头发，该药剂包括化妆品载体和至少一种符合式(I)的化合物。