2-{2-氯-6-羟基-5-[2-甲基喹啉-8-基氨甲基]-3-氧代-3H-呫吨-9-基}苯甲酸磺酸 | 905982-78-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 中文名称: 2-{2-氯-6-羟基-5-[2-甲基喹啉-8-基氨甲基]-3-氧代-3H-呫吨-9-基}苯甲酸磺酸
• 英文名称: 2-(2-chloro-6-hydroxy-5-[(2-methylquinolin-8-ylamino)methyl]-3-oxo-3H-xanthen-9-yl)benzoic acid
• 英文别名: 2-{2-chloro-6-hydroxy-5-[(2-methylquinolin-8-ylamino)methyl]-3-oxo-3H-xanthen-9-yl}benzoic acid；2-{2-chloro-6-hydroxy-5-[(2-methyl-quinolin-8-ylamino)-methyl]-3-oxo-3H-xanthen-9-yl}-benzoic acid；2-{2-Chloro-6-hydroxy-5-[2-methylquinolin-8-ylaminomethyl]-3-oxo-3H-xanthen-9-YL}benzoic acid；2-[2-chloro-6-hydroxy-5-[[(2-methylquinolin-8-yl)amino]methyl]-3-oxoxanthen-9-yl]benzoic acid
• CAS: 905982-78-7
• 化学式: C₃₁H₂₁ClN₂O₅
• 分子量: 536.971
• InChiKey: BNCTXHMCLLLOAB-UHFFFAOYSA-N

物化性质

• 熔点：
  190-192 °C (decomp)
• 沸点：
  783.1±60.0 °C(Predicted)
• 密度：
  1.57±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  39
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  109
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-{2-氯-6-羟基-5-[2-甲基喹啉-8-基氨甲基]-3-氧代-3H-呫吨-9-基}苯甲酸磺酸 在 盐酸 、 sodium hydroxide 、 sodium nitrite 作用下， 以 甲醇 、 水 为溶剂， 以39%的产率得到2-{2-chloro-6-hydroxy-5-[((2-methylquinolin-8-yl)(nitroso)amino)-methyl]-3-oxo-3H-xanthen-9-yl}-benzoic acid
  参考文献：
  名称：

  WO2007/149105

  摘要：

  公开号：
• 作为产物：
  描述：

  8-氨基喹哪啶 在 sodium tetrahydroborate 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 生成 2-{2-氯-6-羟基-5-[2-甲基喹啉-8-基氨甲基]-3-氧代-3H-呫吨-9-基}苯甲酸磺酸
  参考文献：
  名称：

  WO2007/149105

  摘要：

  公开号：

文献信息

• Inhibitors of Bacterial Nitric Oxide Synthase, and Related Screening Methods
  申请人：Lippard Stephen J.

  公开号：US20110201042A1

  公开（公告）日：2011-08-18

  The invention relates in part to compounds that act as highly nitric oxide (NO)-specific turn-on fluorescent probes. The present invention also relates to the use of these fluorescein-based sensors to screen selectively for inhibitors of bacterial nitric oxide synthase (bNOS). Compounds of the present invention readily detect nitric oxide produced in vivo. Therefore they can be used in an assay that measures NO production by bNOS. Using a sensor of the invention one can screen libraries of small molecules for inhibitors of bNOS.

  本发明部分涉及作为高度一氧化氮（NO）特异性开关荧光探针的化合物。本发明还涉及使用这些以荧光素为基础的传感器有选择地筛选细菌一氧化氮合酶（bNOS）抑制剂。本发明的化合物可以轻松检测体内产生的一氧化氮。因此，它们可用于测量bNOS产生的NO的测定中。使用本发明的传感器，可以对小分子库进行筛选以寻找bNOS的抑制剂。
• Mechanism of Nitric Oxide Reactivity and Fluorescence Enhancement of the NO-Specific Probe CuFL1
  作者：Lindsey E. McQuade、Michael D. Pluth、Stephen J. Lippard

  DOI：10.1021/ic101054u

  日期：2010.9.6

  The mechanism of the reaction of CuFL1 (FL1 = 2-2-chloro-6-hydroxy-5-[(2-methylquinolin-8-ylamino)methyl]-3-oxo-3H-xanthen-9-yl}benzoic acid) with nitric oxide (NO) to form the N-nitrosated product FL1-NO in buffered aqueous solutions was investigated. The reaction is first-order in [CuFL1], [NO], and [OH-]. The observed rate saturation at high base concentrations is consistent with a mechanism in which the protonation state of the secondary amine of the ligand is important for reactivity. This information provides a rationale for designing faster-reacting probes by lowering the pk(a) of the secondary amine. Activation parameters for the reaction of CuFL1 with NO indicate an associative mechanism (Delta S-double dagger = -120 +/- 10 J/mol.K) with a modest thermal barrier (Delta H-double dagger = 41 +/- 2 kJ/mol; E-a = 43 +/- 2 kJ/mol). Variable-pH electron paramagnetic resonance experiments reveal that, as the secondary amine of CuFL1 is deprotonated, electron density shifts to yield a new spin-active species having electron density localized on the deprotonated amine nitrogen atom. This result suggests that FL1-NO formation occurs when NO attacks the deprotonated secondary amine of the coordinated ligand, followed by inner-sphere electron transfer to Cu(II) to form Cu(I) and release of FL1-NO from the metal.
• FLUORESCEIN BASED SENSORS FOR TRACKING NITRIC OXIDE IN LIVE CELLS
  申请人：Lippard Stephen J.

  公开号：US20090017552A1

  公开（公告）日：2009-01-15

  The present invention is directed, in part, to coordination complexes for detecting analytes, and methods of making and using the same.
• US7494821B2
  申请人：——

  公开号：US7494821B2

  公开（公告）日：2009-02-24
• US8709743B2
  申请人：——

  公开号：US8709743B2

  公开（公告）日：2014-04-29