2-甲基-2-丙基[(2S)-6-乙酰氨基-1-氧代-1-{[2-氧代-4-(三氟甲基)-2H-苯并吡喃-7-基]氨基}-2-己烷基]氨基甲酸酯 | 787549-23-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 2-甲基-2-丙基[(2S)-6-乙酰氨基-1-氧代-1-{[2-氧代-4-(三氟甲基)-2H-苯并吡喃-7-基]氨基}-2-己烷基]氨基甲酸酯
• 中文别名: 4,7-环氧-1H-环丁二烯并[b]吲哚(9CI)
• 英文名称: (S)-[5-acetylamino-1-(2-oxo-4-trifluoromethyl-2H-chromen-7-ylcarbamoyl)pentyl]carbamic acid tert-butyl ester
• 英文别名: BATCP；tert-butyl N-[(2S)-6-acetamido-1-oxo-1-[[2-oxo-4-(trifluoromethyl)chromen-7-yl]amino]hexan-2-yl]carbamate
• CAS: 787549-23-9
• 化学式: C₂₃H₂₈F₃N₃O₆
• 分子量: 499.487
• InChiKey: NVKNRJCOVHAZDK-KRWDZBQOSA-N

物化性质

• 溶解度：
  在DMSO中的溶解度为16mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  123
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  N^e-乙酰基-N^a-Boc-L-赖氨酸 、 香豆素 151 在 吡啶 、 三氯氧磷 作用下， 反应 1.0h， 以54%的产率得到2-甲基-2-丙基[(2S)-6-乙酰氨基-1-氧代-1-{[2-氧代-4-(三氟甲基)-2H-苯并吡喃-7-基]氨基}-2-己烷基]氨基甲酸酯
  参考文献：
  名称：

  Subtype Selective Substrates for Histone Deacetylases

  摘要：

  To probe the steric requirements for deacylation, we synthesized lysine-derived small molecule substrates and examined structure -reactivity relationships with various histone deacetylases. Rat liver, human HeLa, and human recombinant class I and II histone deacetylases (HDACs) as well as human recombinant NAD(+)-dependent SIRT1 (class III enzyme) were used in these studies. A benzyloxycarbonyl substituent on the alpha-amino group yielded the highest conversion rates. Replacing the epsilon-acetyl group with larger lipophilic acyl substituents led to a pronounced decrease in conversion by class I and II enzymes; the class III enzyme displayed a greater tolerance. Incubations with recombinant FLAG-tagged human HDACs 1, 3, and 6 showed a distinct subtype selectivity among small molecule substrates. The subtype selectivity of HDAC inhibitors could be predicted with these substrates and an easily obtainable mixture of HDAC subtypes.

  DOI：

  10.1021/jm0497592

文献信息

• HAPLOID EMBRYOGENESIS
  申请人：Stichting Wageningen Research

  公开号：EP3571926A1

  公开（公告）日：2019-11-27

  A switch to haploid embryogenesis is controlled by the activity of histone deacetylases (HDACs). Blocking HDAC activity with HDAC inhibitors (HDACi), e.g. trichostatin A (TSA), in Brassica napus, B. rapa, B. oleracea, Arabidopsis thaliana and Capsicum annuum male gametophytes leads to a large increase in the proportion of cells that undergo embryogenic growth. In B. napus, treatment with one specific HDACi (SAHA) improves the conversion (i.e. germination) of these embryos into seedlings. Existing methods of culturing microspores of angiosperm plants following stress to produce haploid embryos, haploid plants and double haploid plants can be improved by adding HDACi to the culture medium. Advantageously, species hitherto recalcitrant to haploid embryogenesis via microspore culture are rendered useful when using HDACi. Haploid and double haploid plants are of industrial application in the plant breeding programmes.

  单倍体胚胎发生的转变受组蛋白去乙酰化酶（HDAC）活性的控制。用 HDAC 抑制剂（HDACi），如三氯靛酚 A（TSA），阻断甘蓝型油菜（Brassica napus）、莴苣（B. rapa）、油菜（B. oleracea）、拟南芥（Arabidopsis thaliana）和辣椒（Capsicum annuum）雄配子体中 HDAC 的活性，会导致发生胚胎生长的细胞比例大幅增加。在油菜中，用一种特定的 HDACi（SAHA）处理可提高这些胚胎向幼苗的转化（即发芽）。通过在培养基中添加 HDACi，可以改进在胁迫后培养被子植物小孢子以产生单倍体胚、单倍体植株和双单倍体植株的现有方法。更有利的是，迄今为止对通过小孢子培养产生单倍体胚胎效果不佳的物种在使用 HDACi 后也变得有用。单倍体和双单倍体植物在植物育种计划中具有工业应用价值。
• Method for producing haploid, dihaploid and doubled haploid plants by isolated microspore culture
  申请人：Vilmorin & Cie

  公开号：US11026381B2

  公开（公告）日：2021-06-08

  The present invention relates to a method for producing haploid, dihaploid, polyhaploid and/or doubled haploid plants of the family Cucurbitaceae from isolated microspores, wherein said method comprises a) culturing isolated microspores to obtain embryos competent for plant regeneration, wherein the microspores have been isolated from plant material of a donor plant of the family Cucurbitaceae; and b) regenerating plants from the embryos; wherein step (a) comprises contacting the microspores with one or more inhibitor of histone deacetylase (HDACi) and one or more polyamine. The present invention also relates to a method for producing haploid, dihaploid, polyhaploid and/or doubled haploid embryos, to related kits and compositions, and to plants obtained according to the methods.

  本发明涉及一种从分离的小孢子中生产葫芦科单倍体、二单倍体、多单倍体和/或加倍单倍体植株的方法，其中所述方法包括 a) 培养分离的小孢子以获得可用于植株再生的胚，其中所述小孢子是从葫芦科供体植株的植物材料中分离的；其中步骤(a)包括将小孢子与一种或多种组蛋白去乙酰化酶抑制剂（HDACi）和一种或多种多胺接触。本发明还涉及一种生产单倍体、二单倍体、多单倍体和/或加倍单倍体胚的方法，涉及相关试剂盒和组合物，以及根据该方法获得的植物。
• HISTONE DEACETYLASE 6 SELECTIVE INHIBITORS FOR THE TREATMENT OF BONE DISEASE
  申请人：The General Hospital Corporation

  公开号：EP2734500A2

  公开（公告）日：2014-05-28
• METHOD FOR PRODUCING HAPLOID, DIHAPLOID AND DOUBLED HAPLOID PLANTS BY ISOLATED MICROSPORE CULTURE
  申请人：Vilmorin & Cie

  公开号：EP3328185B1

  公开（公告）日：2020-06-24
• TREATMENT AND PREVENTION OF NEURODEGENERATIVE DISEASES
  申请人：Maes Tamara

  公开号：US20100247543A1

  公开（公告）日：2010-09-30

  The treatment and prevention of neurodegenerative diseases by repression of the transcriptional complex that silences the promoter of the UCHL1 gene.