(2S)-2-氨基-3-(5-溴-1H-吲哚-3-基)丙酸 | 25197-99-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: (2S)-2-氨基-3-(5-溴-1H-吲哚-3-基)丙酸
• 中文别名: 四氢呋喃均聚醚；5-溴-L-色氨酸；L-5-溴色氨酸
• 英文名称: 5-bromo-L-tryptophan
• 英文别名: L-5-bromotryptophan；5-bromotryptophan；5-bromo-DL-tryptophan；(2S)-2-azaniumyl-3-(5-bromo-1H-indol-3-yl)propanoate
• CAS: 25197-99-3
• 化学式: C₁₁H₁₁BrN₂O₂
• 分子量: 283.125
• InChiKey: KZDNJQUJBMDHJW-VIFPVBQESA-N

物化性质

• 熔点：
  251 °C
• 沸点：
  495.8±45.0 °C(Predicted)
• 密度：
  1.704±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  79.1
• 氢给体数：
  3
• 氢受体数：
  3

安全信息

• 危险性防范说明：
  P280
• 危险性描述：
  H302,H317
• 储存条件：
  室温下应存放在干燥且密封的环境中。

制备方法与用途

5-溴-L-色氨酸是一种α-氨基酸衍生物，在Semenospongia sp.中被发现。

反应信息

• 作为反应物：
  描述：

  (2S)-2-氨基-3-(5-溴-1H-吲哚-3-基)丙酸 以81%的产率得到N-叔丁氧羰基-5-溴-L-色氨酸
  参考文献：
  名称：

  Somatostatin analogs having a substituted tryptophyl residue in position

  摘要：

  公开了公式##STR1##的十四肽，其中A代表L、D或DL 5-或6-氟、溴、氯或碘色氨酸基，或其治疗上可接受的酸盐，公开了它们的制备和制备中间体。这些十四肽对抑制生长激素的释放很有用。还公开了它们的使用的组合物和方法。

  公开号：

  US04224199A1
• 作为产物：
  描述：

  acetyl-5-bromo-DL-tryptophan 在 cobalt(II) chloride hexahydrate 、 acylase I from porcine kidney 作用下， 以 aq. phosphate buffer 为溶剂， 反应 108.0h， 以20%的产率得到(2S)-2-氨基-3-(5-溴-1H-吲哚-3-基)丙酸
  参考文献：
  名称：

  Discovery of 7-[¹⁸F]Fluorotryptophan as a Novel Positron Emission Tomography (PET) Probe for the Visualization of Tryptophan Metabolism in Vivo

  摘要：

  Tryptophan and its metabolites are involved in different physiological and pathophysiological processes. Consequently, positron emission tomography (PET) tracers addressing tryptophan metabolic pathways should allow the detection of different pathologies like neurological disorders and cancer. Herein we report an efficient method for the preparation of fluorotryptophans labeled in different positions with F-18 and their biological evaluation. 4-7-[F-18]Fluorotryptophans ([F-18]FTrps) were prepared according to a modified protocol of alcohol-enhanced Cu-mediated radiofluorination in 30-53% radiochemical yields. In vitro experiments demonstrated high cellular uptake of 4-7[F-18]FTrps in different tumor cell lines. 4, 5-, and 6-[F-18]FTrps, although stable in vitro, suffered from rapid in vivo defluorination. In contrast, 7-[F-18]FTrp demonstrated a high in vivo stability and enabled a clear delineation of serotonergic areas and melatonin-producing pineal gland in rat brains. Moreover 7-[F-18]FTrp accumulated in different tumor xenografts in a chick embryo CAM model. Thus, 7-[F-18]FTrp represents a highly promising PET probe for imaging of Trp metabolism.

  DOI：

  10.1021/acs.jmedchem.7b01245

文献信息

• [EN] AZASULFURYLPEPTIDE-BASED CD36 MODULATORS AND USES THEREOF<br/>[FR] MODULATEURS CD36 À BASE D'AZASULFURYLPEPTIDES ET UTILISATIONS DE CEUX-CI
  申请人：RSEM LTD PARTNERSHIP

  公开号：WO2016029324A1

  公开（公告）日：2016-03-03

  Novel azasulfuryl-containing peptidomimetics capable of inhibiting CD36 activity are disclosed. Use of these azasulfuryl-containing peptidomimetics for the treatment of CD36-related diseases, disorders or conditions, including TLR2-mediated inflammatory disease, disorder or condition, and methods of obtaining such azasulfuryl-containing peptidomimetics, are also disclosed.

  揭示了能够抑制CD36活性的新型含氮硫酰基的肽类模拟物。还揭示了利用这些含氮硫酰基的肽类模拟物治疗与CD36相关的疾病、紊乱或状况，包括TLR2介导的炎症性疾病、紊乱或状况的用途，以及获取这种含氮硫酰基的肽类模拟物的方法。
• Novel IDO inhibitors and methods of use thereof
  申请人：Prendergast C. George

  公开号：US20070105907A1

  公开（公告）日：2007-05-10

  Novel indoleamine 2,3-dioxygenase (IDO) inhibitors, compositions comprising the same, and methods of use thereof are disclosed.

  披露了新型的吲哚胺2,3-双加氧酶（IDO）抑制剂，包含该抑制剂的组合物以及使用它们的方法。
• [EN] TAGGABLE HETEROAROMATIC DRUGS AND CONJUGATES THEREOF<br/>[FR] MÉDICAMENTS HÉTÉROAROMATIQUES ÉTIQUETABLES ET LEURS CONJUGUÉS
  申请人：RAMOT AT TEL-AVIV UNIV LTD

  公开号：WO2016203478A1

  公开（公告）日：2016-12-22

  The present invention provides heteroarene-based drag derivatives having a "clickable" ketone group, as well as conjugates of said drug derivatives with targeting moieties capable of binding to extracellular antigens; and pharmaceutical compositions comprising them.

  本发明提供了基于杂环芳烃的具有“可点击”酮基团的药物衍生物，以及与能够结合细胞外抗原的靶向基团结合的所述药物衍生物的共轭物；以及包含它们的药物组合物。
• Lipid probes and uses thereof
  申请人：THE SCRIPPS RESEARCH INSTITUTE

  公开号：US10168342B2

  公开（公告）日：2019-01-01

  Disclosed herein are methods, compositions, probes, assays and kits for identifying a lipid binding protein as a drug binding target. Also disclosed herein are methods, compositions, and probes for mapping a ligand binding site on a lipid binding protein, identification of lipid binding proteins, generating drug-lipid binding protein profiles, high throughput drug screening, and identification of drugs as potential lipid binding protein ligands.

  披露了用于识别脂质结合蛋白作为药物结合靶点的方法、组合物、探针、检测和试剂盒。此外，还披露了用于绘制脂质结合蛋白上的配体结合位点、识别脂质结合蛋白、生成药物-脂质结合蛋白轮廓、高通量药物筛选以及识别作为潜在脂质结合蛋白配体的药物的方法、组合物和探针。
• Facile in Vitro Biocatalytic Production of Diverse Tryptamines
  作者：Allwin D. McDonald、Lydia J. Perkins、Andrew R. Buller

  DOI：10.1002/cbic.201900069

  日期：2019.8

  the product line: Tryptamines are important synthons in bioactive natural products, but general synthetic routes to tryptamine analogues are limited. We present a highly active and promiscuous biosynthetic cascade using an engineered tryptophan synthase (TrpB) and native tryptophan decarboxylase (TDC) capable of producing a diverse set of tryptamines from readily accessible indoles.

  产品线多样化：色胺是生物活性天然产物中的重要合成子，但色胺类似物的一般合成路线有限。我们提出了一种高度活跃且混杂的生物合成级联，使用工程色氨酸合酶（TrpB）和天然色氨酸脱羧酶（TDC），能够从容易获得的吲哚中产生多种色胺。