3-羧基-5-羟基苯甲醛 | 1022160-01-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-羧基-5-羟基苯甲醛
• 英文名称: 3-carboxy-5-hydroxybenzaldehyde
• 英文别名: 3-formyl-5-hydroxybenzoic acid；3-Formyl-5-hydroxybenzoic acid
• CAS: 1022160-01-5
• 化学式: C₈H₆O₄
• 分子量: 166.133
• InChiKey: YBIDDVOKTAHFOE-UHFFFAOYSA-N

物化性质

• 熔点：
  193 °C
• 沸点：
  407.7±35.0 °C(Predicted)
• 密度：
  1.482±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-羧基-5-羟基苯甲醛 在 盐酸 作用下， 以 水 为溶剂， 生成 (RS)-3-carboxy-5-hydroxyphenylglycine
  参考文献：
  名称：

  Structure-activity relationships of new agonists and antagonists of different metabotropic glutamate receptor subtypes

  摘要：

  1 We investigated the agonist and atagonist activities of 22 new phenylglycine and phenylalamine derivatives for metabotropic glutamate receptors (mGluRs) by examining their effects on the signal transduction of mGluR(1), mGluR(2) and mGluR(6) subtypes expressed in Chinese hamster ovary cells. This analysis revealed several structural characteristics that govern receptor subtype specificity of the agonist and antagonist activities of phenylglycine derivatives.2 Hydroxyphenylglycine derivatives possessed either an agonist activity on mGluR(1) mGluR(6) or an antagonist activity on mGluR(1).3 Carboxyphenylglycine derivatives showed an agonist activity on mGluR(2) but an antagonist activity on mGluR(1).4 alpha-Methylation or alpha-ethylation of the carboxyphenylglycine derivatives converts the agonist property For mGluR(2) to an antagonist property, thus producing antagonists at both mGluR(1) and mGluR(2).5 Structurally-corresponding phenylalanine derivatives showed little or no agonist or antagonist activity on any subtypes of the receptors.6 This investigation demonstrates that the nature and positions of side chains and ring substituents incorporated into the phenylglycine structure are critical in determining the agonist and antagonist activities of members of this group of compounds on different subtypes of the mGluR family.7 We also tested two alpha-methyl derivatives of mGluR agonists. (2S, 1'S, 2'S)-2-(2-Carboxycyciopropyl)glycine (L-CCG-I) is a potent agonist for mGluR(2) but alpha-methylation of this compound changes its activity to that of an mGluR(2)-selective antagonist. In contrast, alpha-methylation of L-2-amino-4-phosphonobutyrate (L-AP4) results in retention of an agonist activity on mCluR(6). Thus, alpha-methylation produces different effects, depending on the chemical structures of lead compounds and/or on the subtype of mGluR tested.

  DOI：

  10.1111/j.1476-5381.1996.tb15312.x
• 作为产物：
  描述：

  3-苄氧基-5-甲酰基苯甲酸 在 三氟乙酸 作用下， 以72%的产率得到3-羧基-5-羟基苯甲醛
  参考文献：
  名称：

  de novo Design and synthesis of N-benzylanilines as new candidates for VEGFR tyrosine kinase inhibitors

  摘要：

  N-苄基苯胺类化合物被设计并合成作为血管内皮生长因子（VEGF）-2抑制剂，采用基于VEGFR-2激酶域的X射线结构的新药设计系统。在合成的化合物中，化合物3显示出对VEGFR-2（KDR）酪氨酸激酶最强的抑制活性，其IC50值为0.57 µM。

  DOI：

  10.1039/b719959g

文献信息

• METHOD FOR IDENTIFYING A COMPOUND USEFUL IN MITIGATING AND/OR THE TREATMENT OF A DISEASE ASSOCIATED WITH ABNORMAL ASTROCYTIC FUNCTION
  申请人：Celica BIOMEDICAL

  公开号：EP3341731B1

  公开（公告）日：2020-01-29
• PRODUCTION OF METAL-ORGANIC FRAMEWORKS
  申请人：Commonwealth Scientific and Industrial Research Organisation

  公开号：US20160347774A1

  公开（公告）日：2016-12-01

  An apparatus for producing metal organic frameworks, comprising: a tubular flow reactor comprising a tubular body into which, in use, precursor compounds which form the metal organic framework are fed and flow, said tubular body including at least one annular loop.
• [EN] METHOD FOR IDENTIFYING A COMPOUND USEFUL IN MITIGATING AND/OR THE TREATMENT OF A DISEASE ASSOCIATED WITH ABNORMAL ASTROCYTIC FUNCTION<br/>[FR] PROCÉDÉ POUR IDENTIFIER UN COMPOSÉ UTILE POUR L'ATTÉNUATION ET/OU LE TRAITEMENT D'UNE MALADIE ASSOCIÉE À UNE FONCTION ASTROCYTIQUE ANORMALE
  申请人：CELICA BIOMEDICAL

  公开号：WO2017060367A1

  公开（公告）日：2017-04-13

  The present invention pertains to a method for identifying a compound that can be used in mitigating and/or the treatment of a disease associated with abnormal astrocytic function, said method comprising: (i) providing a compound; (ii) determining whether said compound is a ligand for the GPR81 receptor by determining said compound's binding energy with the GPR81 receptor using molecular dynamics (MD) simulations and comparing said binding energy to the binding energy determined for a reference compound (such as L-lactate) with the GPR81 receptor; and (iii) if said compound is determined to be a ligand for the GPR81 receptor, bringing said compound in contact with a living astrocyte and determining the cAMP level in said astrocyte contacted with said compound. The present invention further pertains to an agent elevating the cAMP level in astrocytes for use in mitigating and/or in the treatment of a disease associated with abnormal astrocytic function.
• de novo Design and synthesis of N-benzylanilines as new candidates for VEGFR tyrosine kinase inhibitors
  作者：Masaharu Uno、Hyun Seung Ban、Wataru Nabeyama、Hiroyuki Nakamura

  DOI：10.1039/b719959g

  日期：——

  N-Benzylanilines were designed and synthesized as vascular endothelial growth factor (VEGF)-2 inhibitors using de novo drug design systems based on the X-ray structure of VEGFR-2 kinase domain. Among compounds synthesized, compound 3 showed the most potent inhibitory activity toward VEGFR-2 (KDR) tyrosinekinase and its IC50 value was 0.57 µM.

  N-苄基苯胺类化合物被设计并合成作为血管内皮生长因子（VEGF）-2抑制剂，采用基于VEGFR-2激酶域的X射线结构的新药设计系统。在合成的化合物中，化合物3显示出对VEGFR-2（KDR）酪氨酸激酶最强的抑制活性，其IC50值为0.57 µM。
• Structure-activity relationships of new agonists and antagonists of different metabotropic glutamate receptor subtypes
  作者：N. Sekiyama、Y. Hayashi、S. Nakanishi、D.E. Jane、H-W. Tse、E.F. Birse、J.C. Watkins

  DOI：10.1111/j.1476-5381.1996.tb15312.x

  日期：1996.4

  1 We investigated the agonist and atagonist activities of 22 new phenylglycine and phenylalamine derivatives for metabotropic glutamate receptors (mGluRs) by examining their effects on the signal transduction of mGluR(1), mGluR(2) and mGluR(6) subtypes expressed in Chinese hamster ovary cells. This analysis revealed several structural characteristics that govern receptor subtype specificity of the agonist and antagonist activities of phenylglycine derivatives.2 Hydroxyphenylglycine derivatives possessed either an agonist activity on mGluR(1) mGluR(6) or an antagonist activity on mGluR(1).3 Carboxyphenylglycine derivatives showed an agonist activity on mGluR(2) but an antagonist activity on mGluR(1).4 alpha-Methylation or alpha-ethylation of the carboxyphenylglycine derivatives converts the agonist property For mGluR(2) to an antagonist property, thus producing antagonists at both mGluR(1) and mGluR(2).5 Structurally-corresponding phenylalanine derivatives showed little or no agonist or antagonist activity on any subtypes of the receptors.6 This investigation demonstrates that the nature and positions of side chains and ring substituents incorporated into the phenylglycine structure are critical in determining the agonist and antagonist activities of members of this group of compounds on different subtypes of the mGluR family.7 We also tested two alpha-methyl derivatives of mGluR agonists. (2S, 1'S, 2'S)-2-(2-Carboxycyciopropyl)glycine (L-CCG-I) is a potent agonist for mGluR(2) but alpha-methylation of this compound changes its activity to that of an mGluR(2)-selective antagonist. In contrast, alpha-methylation of L-2-amino-4-phosphonobutyrate (L-AP4) results in retention of an agonist activity on mCluR(6). Thus, alpha-methylation produces different effects, depending on the chemical structures of lead compounds and/or on the subtype of mGluR tested.