N-(10-aminodecyl)-9α-fluoro-11β,17α-dihydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carboxamide | 352690-33-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: N-(10-aminodecyl)-9α-fluoro-11β,17α-dihydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carboxamide
• 英文别名: (8S,9R,10S,11S,13S,14S,16R,17R)-N-(10-aminodecyl)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthrene-17-carboxamide
• CAS: 352690-33-6
• 化学式: C₃₁H₄₉FN₂O₄
• 分子量: 532.739
• InChiKey: QVWPEURGLLGBJD-SASCWTSFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  38
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  113
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  gibberellin A₃ 、 N-(10-aminodecyl)-9α-fluoro-11β,17α-dihydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carboxamide 在 O-Benzotriazol-1-yl-N,N,N',N'-bis(tetramethylene)uronium hexafluorophosphate 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.75h， 以56.9%的产率得到N-[10-(9α-fluoro-11β,17α-dihydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carboxamido)decyl]gibberellamide
  参考文献：
  名称：

  Syntheses of Dexamethasone Conjugates of the Phytohormones Gibberellin A3 and 24-Epicastasterone

  摘要：

  描述了合成N-[10-(9α-氟-11β,17α-二羟基-16α-甲基-3-氧代-5-烯-17β-羧酰胺)癸基]赤霉素（7）和6-[({N-[10-(9α-氟-11β,17α-二羟基-16α-甲基-3-氧代-5-烯-17β-羧酰胺)癸基]氨基}甲氧基)亚胺]-24-表雄甾酮（10）。用[(苯并三唑-1-基)氧基]双(吡咯烷-1-基)甲基六氟磷酸盐（HBPyU）作为偶联剂，将赤霉素酸以及24-表雄甾酮-O-(羧甲基)肟与N-(10-氨基癸基)-9α-氟-11β,17α-二羟基-16α-甲基-3-氧代-5-烯-17β-羧酰胺（4）反应。赤霉素酸结合物7也通过琥珀酰亚胺基赤霉素酸盐6与胺4的偶联反应合成。

  DOI：

  10.1135/cccc20020103
• 作为产物：
  描述：

  地塞米松 在 硫酸 、 高碘酸 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 乙酸乙酯 为溶剂， 反应 44.0h， 生成 N-(10-aminodecyl)-9α-fluoro-11β,17α-dihydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carboxamide
  参考文献：
  名称：

  Syntheses of Dexamethasone Conjugates of the Phytohormones Gibberellin A3 and 24-Epicastasterone

  摘要：

  描述了合成N-[10-(9α-氟-11β,17α-二羟基-16α-甲基-3-氧代-5-烯-17β-羧酰胺)癸基]赤霉素（7）和6-[({N-[10-(9α-氟-11β,17α-二羟基-16α-甲基-3-氧代-5-烯-17β-羧酰胺)癸基]氨基}甲氧基)亚胺]-24-表雄甾酮（10）。用[(苯并三唑-1-基)氧基]双(吡咯烷-1-基)甲基六氟磷酸盐（HBPyU）作为偶联剂，将赤霉素酸以及24-表雄甾酮-O-(羧甲基)肟与N-(10-氨基癸基)-9α-氟-11β,17α-二羟基-16α-甲基-3-氧代-5-烯-17β-羧酰胺（4）反应。赤霉素酸结合物7也通过琥珀酰亚胺基赤霉素酸盐6与胺4的偶联反应合成。

  DOI：

  10.1135/cccc20020103

文献信息

• Preparation and Biological Activity of Molecular Probes to Identify and Analyze Jasmonic Acid-binding Proteins
  作者：Yusuke JIKUMARU、Tadao ASAMI、Hideharu SETO、Shigeo YOSHIDA、Tadashi YOKOYAMA、Naomi OBARA、Morifumi HASEGAWA、Osamu KODAMA、Makoto NISHIYAMA、Kazunori OKADA、Hideaki NOJIRI、Hisakazu YAMANE

  DOI：10.1271/bbb.68.1461

  日期：2004.1

  Several types of jasomonic acid (JA) derivatives, including JA–amino acid conjugates, a JA–biotin conjugate, a JA–dexamethasone heterodimer, and a JA–fluoresceine conjugate, were prepared as candidates for molecular probes to identify JA-binding proteins. These JA derivatives, excepting the JA–fluoresceine conjugate, exhibited significant biological activities in a rice seedling assay, a rice phytoalexin-inducing assay, and/or a soybean phenylalanine ammonia-lyase-inducing assay. These JA derivatives could therefore be useful probes for identifying JA-binding proteins. The activity spectra of the prepared compounds were different from each other, suggesting that different types of JA receptors were involved in the perception of JA derivatives in the respective bioassays.

  几种类型的茉莉酸（JA）衍生物被制备为识别JA结合蛋白的分子探针候选者，包括JA-氨基酸结合物、JA-生物素结合物、JA-氟莱赛因结合物和JA-地塞米松异二聚体。这些JA衍生物（排除JA-氟莱赛因结合物）在水稻幼苗测定、水稻植物防御素诱导测定和/或大豆苯丙氨酸氨解酶诱导测定中表现出显著的生物活性。因此，这些JA衍生物可以作为识别JA结合蛋白的有用探针。所制备化合物的活性谱各不相同，表明在各自的生物测定中涉及了不同类型的JA受体对JA衍生物的感知。
• Synthesis of a β-Estradiol-Biotin Chimera that Potently Heterodimerizes Estrogen Receptor and Streptavidin Proteins in a Yeast Three-Hybrid System
  作者：Stephen L. Hussey、Smita S. Muddana、Blake R. Peterson

  DOI：10.1021/ja0293305

  日期：2003.4.1

  Small molecules that dimerize proteins in living cells provide powerful probes of biological processes and have potential as tools for the identification of protein targets of natural products. We synthesized 7-alpha-substituted derivatives of beta-estradiol tethered to the natural product biotin to regulate heterodimerization of estrogen receptor (ER) and streptavidin (SA) proteins expressed as components of a yeast three-hybrid system. Addition of an estradiol-biotin chimera bearing a 19-atom linker to yeast expressing DNA-bound ER-alpha or ER-beta LexA fusion proteins and wild-type SA protein fused to the B42 activation domain activated reporter gene expression by as much as 450-fold in vivo (10 muM ligand). Comparative analysis of lower affinity Y43A (biotin Kd approximately 100 pM) and W120A (biotin Kd approximately 100 nM) mutants of SA indicated that moderate affinity interactions can be readily detected with this system. Comparison of a 7-alpha-substituted estradiol-biotin chimera with a structurally similar dexamethasone-biotin chimera revealed that yeast expressing ER proteins can detect cognate ligands with up to 5-fold greater potency and 70-fold higher activity than yeast expressing analogous glucocorticoid receptor (GR) proteins. This approach may facilitate the identification of protein targets of biologically active small molecules screened against genetically encoded libraries of proteins expressed in yeast three-hybrid systems.
• A GAL4-based yeast three-hybrid system for the identification of small molecule–target protein interactions
  作者：Debbie C. Henthorn、Albert A. Jaxa-Chamiec、Eric Meldrum

  DOI：10.1016/s0006-2952(02)00884-5

  日期：2002.5

  We report the development of a yeast strain designed for assaying compound-protein interactions through activation of reporter gene expression. Activation of lacZ expression, driven by the GAL4 promoter, has been demonstrated for precedented compound-protein interactions between FK506 and FK506 binding protein 12 (FKBP12) and also between methotrexate (MTX) and dihydrofolate reductase (DHFR). Reporter gene expression was completely abrogated in a competitive manner by the presence of excess FK506 or MTX, respectively. In addition, a strain expressing a mutated DHFR clone with decreased binding affinity for MTX was not capable of activating reporter gene expression. While strain sensitivity is compound-dependent, the minimum compound concentration necessary to drive reporter gene expression was 20 nM for the FK506-FKBP12 interaction. The utility of this strain as a tool for identifying unknown compound-binding proteins has been demonstrated by screening a mouse cDNA library for clones that encode proteins capable of binding MTX. Four library clones of mouse DHFR were identified after screening 5 x 106 clones. The screen background was low and false positives were easily identified, making this yeast system particularly amenable for use in a screening context for novel compound-protein interactions. (C) 2002 Published by Elsevier Science Inc.