(1R,8Z,13S,15R,16R)-13,15,16-trihydroxy-2-oxa-11-azabicyclo[11.3.1]heptadec-8-ene-3,12-dione | 933776-33-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: (1R,8Z,13S,15R,16R)-13,15,16-trihydroxy-2-oxa-11-azabicyclo[11.3.1]heptadec-8-ene-3,12-dione
• CAS: 933776-33-1
• 化学式: C₁₅H₂₃NO₆
• 分子量: 313.351
• InChiKey: NYKXZWSSPWXCMO-VCFHAVPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  116
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1R,8Z,13S,15R,16R)-13,15,16-trihydroxy-2-oxa-11-azabicyclo[11.3.1]heptadec-8-ene-3,12-dione 、 BOC-L-苯丙氨酸 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.08h， 以87%的产率得到[(1R,8Z,13R,15R,16S)-13,16-dihydroxy-3,12-dioxo-2-oxa-11-azabicyclo[11.3.1]heptadec-8-en-15-yl] (2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoate
  参考文献：
  名称：

  WO2008/98138

  摘要：

  公开号：
• 作为产物：
  描述：

  在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 咪唑 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 7.25h， 生成 (1R,8Z,13S,15R,16R)-13,15,16-trihydroxy-2-oxa-11-azabicyclo[11.3.1]heptadec-8-ene-3,12-dione
  参考文献：
  名称：

  Synthetic Macrolides that Inhibit Breast Cancer Cell Migration in Vitro

  摘要：

  The design and synthesis of a series of natural product-like synthetic macrolides built upon a quinic acid-containing scaffold are described. Three of the macrolides ( 1, 3, and 6) have been shown to inhibit 4T1 breast cancer cell migration with low nanomolar to sub-micromolar IC50 values ( 77, 525, and 550 nM, respectively) in complementary assays including a quantitative cell migration assay and a semiquantitative wound healing assay.

  DOI：

  10.1021/ja068538d

文献信息

• SYNTHETIC MACROCYCLIC COMPOUNDS AND METHODS FOR TREATING CANCER
  申请人：Bewley Carole A.

  公开号：US20120128657A1

  公开（公告）日：2012-05-24

  Disclosed herein are macrocyclic compounds that are effective to inhibit cell migration. In one embodiment, the compounds have the structure: or any pharmaceutically acceptable salt or solvate thereof, wherein: m is 0 or 1; R 1 , R 2 and R 3 independently are H, aralkyl, acyl, lower alkyl or silyl; X is —C(O)N(R 4 )— or —C(S)N(R 4 )—; —C(O)—; —C(S)—; Y is —OC(O)—; —OC(O)N(R 5 )—; —N(R 5 )C(O)—; or —OC(O)O—; G comprises a saturated or unsaturated aliphatic chain having from 2 to about 10 atoms in the chain, the chain optionally including 1, 2, or 3 heteroatoms; the chain optionally being substituted with 1, 2 or 3 substituents independently selected from lower alkyl, —OR 6 , epoxy, aziridinyl, cyclopropyl, —NR 7 R 8 and halo; R 4 , R 5 , R 6 , R 7 and R 8 independently are selected from H, lower alkyl and acyl. Also disclosed are methods for making and using compounds as well as pharmaceutical compositions including one or more of the disclosed macrocycles.