2-(fluoresceinylamino)-4,6-dichloro-s-triazine | 93265-91-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2-(fluoresceinylamino)-4,6-dichloro-s-triazine
• 英文别名: 5-[(4,6-Dichloro-1,3,5-triazin-2-yl)amino]-2-(3-hydroxy-6-oxo-xanthen-9-yl)benzoic acid；5-[(4,6-dichloro-1,3,5-triazin-2-yl)amino]-2-(3-hydroxy-6-oxoxanthen-9-yl)benzoic acid
• CAS: 93265-91-9
• 化学式: C₂₃H₁₂Cl₂N₄O₅
• 分子量: 495.278
• InChiKey: XUKNSVZRTGCRPH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  34
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  135
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (R)-4-{(S)-2-[(R)-2-((3R,4R,5S,6R)-3-Acetylamino-2,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy)-propionylamino]-6-amino-hexanoylamino}-4-carbamoyl-butyric acid 、 2-(fluoresceinylamino)-4,6-dichloro-s-triazine 以60%的产率得到
  参考文献：
  名称：

  HIEBERT, C. K.;KOPP, W. C.;RICHERSON, H. B.;BARFKNECHT, C. F., J. MED. CHEM., 31,(1988) N 10, C. 2022-2024

  摘要：

  DOI：

文献信息

• A Combinatorial Method for Solution-Phase Synthesis of Labeled Bivalent β-Turn Mimics
  作者：Yu Angell、Dianjun Chen、Fouad Brahimi、H. Uri Saragovi、Kevin Burgess

  DOI：10.1021/ja074717z

  日期：2008.1.1

  Piperidine-functionalized, 1,4-disubstituted-1,2,3-triazoles of generic structure 1 were conceived as "minimalist" mimics of peptidic beta-turn structures. Key features of these molecules include (i) the possibility of incorporating amino acid side chains corresponding to many of the protein amino acids; (ii) a close correspondence of separations of these side chains to i + 1 to i + 2 residues in turns; (iii) facile adjustment of the side-chain vectors on docking while only influencing two critical degrees of freedom; and (iv) some electrostatic polarity. Fifteen monomers of this type were made via copper-mediated cycloaddition reactions. Solution-phase methodologies were devised to assemble these monomers into bivalent compounds in high purity states (typically >85%) so that they could be used in first-pass biological assays without further purification. The skeleton for forming these bivalent compounds is triazine-based. There is a third site which allowed for introduction of a fluorescent label (library of compounds 2) or an alkyne-functionalized triethylene glycol chain (library of compounds 3) included to promote water-solubility and to allow incorporation of probes via copper-mediated cycloaddition reactions. In the event, two 135-membered libraries were prepared, one consisting of compounds 2 and the other of 3. No protecting groups or coupling agents were required; these attributes of the method were important to allow most of the products to be obtained in over 85% purities. The fluorescein-tagged library of compounds 2 was screened in a fluorescence-activated cell sorting (FACS) assay using cells transfected to overexpress one of the following neurotrophin receptors: TrkA, TrkC, and p75. Preliminary findings indicate four compounds 2gm, 2gn, 2gi, and 2gj bound the TrkA receptor selectively; all of these contain a threonine-lysine turn mimic. Thus, a pharmacological probe for the TrkA receptor has been developed.
• HIEBERT, C. K.;KOPP, W. C.;RICHERSON, H. B.;BARFKNECHT, C. F., J. MED. CHEM., 31,(1988) N 10, C. 2022-2024
  作者：HIEBERT, C. K.、KOPP, W. C.、RICHERSON, H. B.、BARFKNECHT, C. F.

  DOI：——

  日期：——
• Synthesis of fluorescent muramyl dipeptide congeners. 2
  作者：C. K. Hiebert、W. C. Kopp、H. B. Richerson、C. F. Barfknecht

  DOI：10.1021/jm00118a029

  日期：1988.10

  Muramyl dipeptide (MDP) analogues were prepared and utilized in the synthesis of new fluorescently labeled MDP derivatives for use as biologic probes. Thus, N alpha-(N-acetylmuramyl)-L-lysyl-D-isoglutamine (Lys-MDP, 4) and N alpha-(N-acetylmuramyl)-L-alanyl-D-isoglutaminyl)-L-lysine [MTP, 5] were synthesized and then reacted with 2-(fluoresceinylamino)-4,6-dichloro-s-triazine (DTAF, 2) to yield the fluorescent adducts, DTAF-Lys-MDP (6) and DTAF-MTP (7). The adjuvant activity of the fluorescent MDP derivatives was determined by the ability of the compounds to promote delayed skin test responses in guinea pigs immunized with ovalbumin (OA) and by evaluating the anti-OA activity of these guinea pigs.
• TARGETED DELIVERY USING TISSUE-SPECIFIC PEPTIDOMIMETIC LIGANDS
  申请人：Templeton Nancy Smyth

  公开号：US20110059161A1

  公开（公告）日：2011-03-10

  Compositions and methods for tissue-specific targeted delivery of therapeutic agents through the use of tissue-specific peptidomimetic ligands are disclosed herein. The ligand comprises a composition of formula A-scaffold-A′ and one or more hydrophobic anchors covalently linked to the scaffold. The A and A′ compounds linked to the scaffold comprise monovalent peptidomimetic compounds wherein each monovalent peptidomimetic compound is selected from the group consisting of fragments IKs, GKs, IDs, GSs, GTs, VSs, TKs, KTs, ARs, KIs, KEs, AEs, GRs, YSs, IRs, and morpholino.
• US8333988B2
  申请人：——

  公开号：US8333988B2

  公开（公告）日：2012-12-18