2-amino-6-hydroxy-2-tetralincarboxylic acid | 84809-70-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-amino-6-hydroxy-2-tetralincarboxylic acid
• 英文别名: 6-hydroxy-2-aminotetralin-2-carboxylic acid；2-Amino-6-hydroxy-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid；2-amino-6-hydroxy-3,4-dihydro-1H-naphthalene-2-carboxylic acid
• CAS: 84809-70-1
• 化学式: C₁₁H₁₃NO₃
• 分子量: 207.229
• InChiKey: CTMHZHQGCDKLCQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  83.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-amino-6-hydroxy-2-tetralincarboxylic acid 在 盐酸 、 sodium hydroxide 、 copper(II) sulfate 作用下， 反应 60.0h， 生成 6-(benzyloxy)-2-<(benzyloxy)carbamido>-2-tetralincarboxylic acid
  参考文献：
  名称：

  两种含有构象受约束的N-末端酪氨酸残基的亮氨酸-脑啡肽类似物的合成和镇痛特性。

  摘要：

  通过经典溶液法合成了亮氨酸脑啡肽的两个类似物，其中末端酪氨酸-1残基已被构象受限的酪氨酸类似物取代，它们在电刺激的豚鼠回肠和小鼠输精管上的鸦片激动剂效力为与亮氨酸脑啡肽相比测定。[（2-氨基-6-羟基-2-四氢萘基）羰基]甘氨酰甘氨酰苯丙氨酰亮氨酸甲酯（3e）中酪氨酸部分自由度的限制导致在mu受体亚型的激动剂活性高7至8倍与亮氨酸脑啡肽相比，豚鼠回肠中的浓度降低了30倍左右。在上述测试中，[（2-氨基-5-羟基-2-茚满基）羰基]-甘氨酰甘氨酰苯丙氨酰亮氨酸甲酯（2e）没有活性。这些结果证明了限制构象柔韧性对受体识别的不同作用。当在sc和icv给药后通过热板试验在小鼠中评估时，两种类似物均不具有任何镇痛特性。

  DOI：

  10.1021/jm00359a024
• 作为产物：
  描述：

  3',4'-dihydro-6'-methoxyspiro-2,5-dione 在 48percent aq. HBr 作用下， 反应 48.0h， 以67%的产率得到2-amino-6-hydroxy-2-tetralincarboxylic acid
  参考文献：
  名称：

  Deltorphin II Analogues with 6-Hydroxy-2-aminotetralin-2-carboxylic Acid in Position 1

  摘要：

  Two approaches to the design of very active and highly selective delta opioid peptides were used to obtain new deltorphin analogues with altered hydrophobic and stereoelectronic properties. Deltorphin II analogues were synthesized with the substitution of Ile instead of Val at positions 5 and 6 in the address domain and 6-hydroxy-2-aminotetralin-2-carboxylic acid (Hat) instead of Tyr(1) in the message domain. In the radioreceptor-binding studies, in which type-specific tritiated opioid ligands were used, (R)- and (S)-Hat-deltorphins exhibited similar K-i values, revealing high delta selectivity. The peptides displayed agonist properties in the in vitro bioassay, with IC50 values in the subnanomolar range in the mouse vas deferens assay and in the micromolar or higher range in the guinea pig ileum assay, again demonstrating a high selectivity toward delta receptors. The agonist property of the new ligands was confirmed by means of [S-35]- GTP gamma S-binding experiments in membranes of the rat frontal cortex.

  DOI：

  10.1021/jm9911534

文献信息

• Homocyclic derivatives
  申请人：Imperial Chemical Industries PLC

  公开号：US04464358A1

  公开（公告）日：1984-08-07

  Compounds of the formula: ##STR1## wherein R.sup.1 stands for hydrogen or a defined hydrocarbyl or halogenoalkenyl radical, R.sup.2 stands for a defined hydrocarbyl, halogenoalkenyl or furylmethyl radical, R.sup.3 is a substituent at position (a) or (b) and stands for a hydroxy or defined alkoxy or alkanoyloxy radical, R.sup.4 stands for a defined alkoxy, cyanoalkoxy or alkenyloxy radical or a defined amino acid residue or peptide residue, and n stands for 1, 2 or 3, and pharmaceutically-acceptable salts thereof. Processes for the manufacture of the compounds. Pharmaceutical compositions comprising one of the compounds and a pharmaceutical diluent or carrier. The compounds are antagonists at the opiate receptors, and most of them are selective .delta.-receptor antagonists.

  化合物的公式为：##STR1## 其中R.sup.1代表氢或定义的烃基或卤代烯基基团，R.sup.2代表定义的烃基，卤代烯基或呋喃甲基基团，R.sup.3是位置（a）或（b）上的取代基，代表羟基或定义的烷氧基或酰基氧基基团，R.sup.4代表定义的烷氧基，氰基烷氧基或烯基氧基基团或定义的氨基酸残基或肽残基，n代表1、2或3，以及其药学上可接受的盐。制备这些化合物的方法。包括其中一种化合物和药学稀释剂或载体的制药组合物。这些化合物是阿片受体拮抗剂，其中大部分是选择性δ受体拮抗剂。
• Lanthionine bridged peptides
  申请人：——

  公开号：US20020165132A1

  公开（公告）日：2002-11-07

  Disclosed are lanthionine bridged peptides having the structure 1 methods of their preparation and their use as pharmacologically active agents.

  所公开的镧系桥接肽具有以下结构 1 其制备方法及其作为药理活性剂的用途。
• Amino-substituted tetralins and related homocyclic compounds
  申请人：IMPERIAL CHEMICAL INDUSTRIES PLC

  公开号：EP0077122B1

  公开（公告）日：1986-05-07
• COMPOSITIONS AND METHODS FOR SKIN CARE
  申请人：During Matthew J.

  公开号：US20100221200A1

  公开（公告）日：2010-09-02

  The present disclosure contemplates compositions and methods for skin care. In some embodiments, the compositions may comprise delta opioid receptor agonists. The skin care composition may comprise peptide delta opioid receptor agonists, non-peptide delta opioid receptor agonists, or combinations thereof. In further embodiments, the peptide delta opioid receptor agonists may be chosen from enkephalins and/or deltorphins. In yet other embodiments, the delta opioid receptor agonists may be conjugated to another molecule. For example, the delta opioid receptor agonist may be conjugated to a lipid in order to facilitate entry across the stratum corneum. Further disclosed herein is the cosmetic use of at least one combination as described above, in a composition suitable for topical application to the skin, as an agent for smoothing out wrinkles and fine lines, such as expression wrinkles.
• US4464358A
  申请人：——

  公开号：US4464358A

  公开（公告）日：1984-08-07