2-(1H-indole-3-carboxamido)acetic acid

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-(1H-indole-3-carboxamido)acetic acid
• 英文别名: 2-(1H-indole-3-carbonylamino)acetic acid
• 化学式: C₁₁H₁₀N₂O₃
• mdl: MFCD09938050
• 分子量: 218.212
• InChiKey: QBGTUKHXPABEHI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  82.2
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,5-二甲基溴苄 、 2-(1H-indole-3-carboxamido)acetic acid 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.08h， 以43%的产率得到2-[1-(3,5-dimethylbenzyl)-1H-indole-3-carboxamido]acetic acid
  参考文献：
  名称：

  Fragment hopping approach directed at design of HIV IN-LEDGF/p75 interaction inhibitors

  摘要：

  We recently identified a series of indole derivatives as active inhibitors of IN-LEDGF/p75 interaction through structure-based pharmacophore models generated from the crystal structure of dimeric catalytic core domain (CCD) of HIV-1 IN in complex with the LEDGF integrase binding domain (IBD). In this paper we used the fragment hopping approach to design small molecules able to prevent the IN-LEDGF/p75 interaction. By means of the proposed approach, we designed novel non-peptidyl compounds that mimic the biological function of some IBD residues and in particular the LEDGF hot spot residues Ile365 and Asp366. The biological results confirmed the importance of several structural requirements for the inhibitory effects of this class of compounds.

  DOI：

  10.3109/14756366.2012.703184
• 作为产物：
  描述：

  methyl N-(1H-indol-3-ylcarbonyl)glycinate 在 lithium hydroxide monohydrate 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以147 mg的产率得到2-(1H-indole-3-carboxamido)acetic acid
  参考文献：
  名称：

  [EN] COMPOSITION FOR PREVENTING OR TREATING CHRONIC KIDNEY DISEASE, COMPRISING COMPOUND THAT INDUCES EXPRESSION OF ANTI-AGING GENE KLOTHO
  [FR] COMPOSITION POUR PRÉVENIR OU TRAITER UNE MALADIE RÉNALE CHRONIQUE, COMPRENANT UN COMPOSÉ QUI INDUIT L'EXPRESSION D'UN GÈNE KLOTHO ANTI-VIEILLISSEMENT
  [KO] 항노화 유전자 KLOTHO의 발현을 유도하는 화합물을 포함하는 만성신장질환의 예방 또는 치료용 조성물

  摘要：

  本发明涉及含有诱导抗衰老基因klotho表达的化合物的慢性肾脏疾病（CKD）预防或治疗配方。根据本发明，用化学式1表示的化合物具有优异的增强与衰老相关的基因Klotho基因表达量的效果，可用作预防、改善或治疗慢性肾脏疾病的药物配方或食品配方。

  公开号：

  WO2022211574A1

文献信息

• COMPOUND FOR INDUCING EXPRESSION OF ANTI-AGING GENE KLOTHO AND USE THEREOF
  申请人：Klotho Sciences

  公开号：EP4039676A1

  公开（公告）日：2022-08-10

  The present invention relates to a compound for inducing the expression of the anti-aging gene klotho and a preparation method therefor. The compound represented by Chemical Formula 1, according to the present invention, has an excellent effect of increasing the expression level of the klotho gene which is a gene associated with aging, and thus can be useful for a pharmaceutical composition, cosmetic composition or food composition for preventing skin aging, inhibiting cellular senescence or preventing, treating alleviating a vascular aging-induced disease or a renal disease.

  本发明涉及一种诱导抗衰老基因 klotho 表达的化合物及其制备方法。根据本发明，化学式 1 所代表的化合物在提高与衰老相关的基因 klotho 的表达水平方面具有极佳的效果，因此可用于药物组合物、化妆品组合物或食品组合物，以防止皮肤衰老、抑制细胞衰老或预防、治疗缓解血管衰老引起的疾病或肾脏疾病。
• [EN] COMPOUND FOR INDUCING EXPRESSION OF ANTI-AGING GENE KLOTHO AND USE THEREOF<br/>[FR] COMPOSÉ DESTINÉ À INDUIRE L'EXPRESSION D'UN GÈNE KLOTHO ANTI-ÂGE ET SON UTILISATION<br/>[KO] 항노화 유전자 KLOTHO의 발현을 유도하는 화합물 및 이의 용도
  申请人：KLOTHO SCIENCES

  公开号：WO2021066608A1

  公开（公告）日：2021-04-08

  본 발명은 항노화 유전자 klotho의 발현을 유도하는 화합물 및 이의 제조방법에 관한 것으로, 본 발명에 따른 화학식 1로 표시되는 화합물은 노화와 관련된 유전자인 Klotho 유전자의 발현량을 향상시키는 효과가 우수하고, 이에 따라 피부 노화 방지, 세포 노화 억제 또는 혈관 노화로 인해 유발되는 질환 또는 신장질환 관련 의 예방, 치료, 개선용 약학 조성물, 화장료 조성물 또는 식품 조성물로 유용할 수 있다.
• Fragment hopping approach directed at design of HIV IN-LEDGF/p75 interaction inhibitors
  作者：Laura De Luca、Stefania Ferro、Francesca Morreale、Frauke Christ、Zeger Debyser、Alba Chimirri、Rosaria Gitto

  DOI：10.3109/14756366.2012.703184

  日期：2013.10.1

  We recently identified a series of indole derivatives as active inhibitors of IN-LEDGF/p75 interaction through structure-based pharmacophore models generated from the crystal structure of dimeric catalytic core domain (CCD) of HIV-1 IN in complex with the LEDGF integrase binding domain (IBD). In this paper we used the fragment hopping approach to design small molecules able to prevent the IN-LEDGF/p75 interaction. By means of the proposed approach, we designed novel non-peptidyl compounds that mimic the biological function of some IBD residues and in particular the LEDGF hot spot residues Ile365 and Asp366. The biological results confirmed the importance of several structural requirements for the inhibitory effects of this class of compounds.
• [EN] COMPOSITION FOR PREVENTING OR TREATING CHRONIC KIDNEY DISEASE, COMPRISING COMPOUND THAT INDUCES EXPRESSION OF ANTI-AGING GENE KLOTHO<br/>[FR] COMPOSITION POUR PRÉVENIR OU TRAITER UNE MALADIE RÉNALE CHRONIQUE, COMPRENANT UN COMPOSÉ QUI INDUIT L'EXPRESSION D'UN GÈNE KLOTHO ANTI-VIEILLISSEMENT<br/>[KO] 항노화 유전자 KLOTHO의 발현을 유도하는 화합물을 포함하는 만성신장질환의 예방 또는 치료용 조성물
  申请人：KLOTHO SCIENCES

  公开号：WO2022211574A1

  公开（公告）日：2022-10-06

  본 발명은 항노화 유전자 klotho의 발현을 유도하는 화합물을 포함하는 만성신장질환((chronic kidney disease, CKD)의 예방 또는 치료용 조성물에 관한 것이다. 본 발명에 따른 화학식 1로 표시되는 화합물은 노화와 관련된 유전자인 Klotho 유전자의 발현량을 향상시키는 효과가 우수하며, 만성신장질환의 예방, 개선 또는 치료용 약학 조성물 또는 식품 조성물로 유용하게 사용될 수 있다.

  本发明涉及含有诱导抗衰老基因klotho表达的化合物的慢性肾脏疾病（CKD）预防或治疗配方。根据本发明，用化学式1表示的化合物具有优异的增强与衰老相关的基因Klotho基因表达量的效果，可用作预防、改善或治疗慢性肾脏疾病的药物配方或食品配方。