amygdalinic acid | 66427-92-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: amygdalinic acid
• 英文别名: D-amygdalinic acid；mandelic acid β-gentiobioside；(2R)-(6-O-(β-D-glucopyranosyl)-β-D-glucopyranosyloxy)-phenylacetic acid；(2R)-2-phenyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyacetic acid
• CAS: 66427-92-7
• 化学式: C₂₀H₂₈O₁₃
• 分子量: 476.435
• InChiKey: IHWHGPUDYPIVLL-BFMJJVGDSA-N

物化性质

• 沸点：
  801.3±65.0 °C(Predicted)
• 密度：
  1.65±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.9
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  216
• 氢给体数：
  8
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  D-扁桃酸 在 甲醇 、 三氟化硼乙醚 、 sodium methylate 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 生成 amygdalinic acid
  参考文献：
  名称：

  Synthesis and evaluation of diverse analogs of amygdalin as potential peptidomimetics of peptide T

  摘要：

  Peptide T (ASTTTNYT) is a promising molecule to prevent the neuro psychometric symptoms of patients suffering AIDS and for the treatment of psoriasis. In order to fully prove its therapeutic benefits, efforts were put forward to design peptidomimetics of the peptide. In this direction, in a recent computational study the natural product amygdalin was identified as a prospective peptidomimetic of the peptide and later proved to exhibit a similar chemotactic profile to the peptide. However, the cyanide moiety of amygdalin provides to the molecule a toxic profile. The present study reports the synthesis of a set of amygdalin analogs lacking the cyanide group with improved chemotactic profiles. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.12.071

文献信息

• USE OF AMYGDALIN ANALOGUES FOR THE TREATMENT OF PSORIASIS
  申请人：Universitat Politecnica de Catalunya

  公开号：EP1847270B1

  公开（公告）日：2010-03-03
• Use of Amygdalin Analogues for the Treatment of Psoriasis
  申请人：Perez Gonzalez Juan Jesus

  公开号：US20110028410A9

  公开（公告）日：2011-02-03

  The compounds of formula (1), wherein n is an integer from 0 to 4; R1 is a radical selected from the group consisting of H, CH 3 , CH 2 -CH 3 , C(CH 3 ) 3 , COOH, CONH 2 and C=CH; R2, R3, R4 and R5 are radicals independently selected from the group consisting of H, F, Cl, Br, (C 1 -C 3 )-alkoxyl and (C 1 -C 4 )-alkyl; and R6 is a radical selected from the group consisting of H, F, Cl, Br, (C 1 -C 3 )-alkoxyl, (C 1 -C 4 )-alkyl, R7, CH=CH-R7 and O-CH 2 -R7; wherein R7 is phenyl or phenyl mono- or independently di-substituted with F, Cl, Br, (C 1 -C 3 )-alkoxyl or (C 1 -C 4 )-alkyl, exhibit a similar chemotactic index to that of amygdalin (natural product whose chemotaxis profile is similar to that of peptide T) and, consequently, are useful for treating inflammatory and/or allergic dermatophathies, such as psoriasis, and are especially much less toxic than amygdalin.
• US7956039B2
  申请人：——

  公开号：US7956039B2

  公开（公告）日：2011-06-07
• Synthesis and evaluation of diverse analogs of amygdalin as potential peptidomimetics of peptide T
  作者：Eyleen Araya、Alex Rodriguez、Jaime Rubio、Alessandro Spada、Jesus Joglar、Amadeu Llebaria、Carmen Lagunas、Andres G. Fernandez、Susanna Spisani、Juan J. Perez

  DOI：10.1016/j.bmcl.2004.12.071

  日期：2005.3

  Peptide T (ASTTTNYT) is a promising molecule to prevent the neuro psychometric symptoms of patients suffering AIDS and for the treatment of psoriasis. In order to fully prove its therapeutic benefits, efforts were put forward to design peptidomimetics of the peptide. In this direction, in a recent computational study the natural product amygdalin was identified as a prospective peptidomimetic of the peptide and later proved to exhibit a similar chemotactic profile to the peptide. However, the cyanide moiety of amygdalin provides to the molecule a toxic profile. The present study reports the synthesis of a set of amygdalin analogs lacking the cyanide group with improved chemotactic profiles. (c) 2005 Elsevier Ltd. All rights reserved.