methyl 5-(dimethylamino)naphthalene-1-sulfonate | 121364-63-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: methyl 5-(dimethylamino)naphthalene-1-sulfonate
• CAS: 121364-63-4
• 化学式: C₁₃H₁₅NO₃S
• 分子量: 265.333
• InChiKey: ZYQDPLFSVDBZCS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 5-(dimethylamino)naphthalene-1-sulfonate 、 三氟甲烷磺酸甲酯 以 二氯甲烷 为溶剂， 反应 24.0h， 以75%的产率得到
  参考文献：
  名称：

  二氯甲烷中溴离子对 SN2 的置换——反胶束的作用

  摘要：

  反胶束系统作为反应介质很受关注，因为它们是生物区室化、酶催化和生物分子分离的强大模型。离子表面活性剂在非极性溶剂中的溶液可能含有反胶束，但它们也可能含有离子对或小团簇，带有水合水。我们研究了阳离子四烷基溴化铵盐（鎓盐）在 CH2Cl2 溶液中的双分子反应，例如十六烷基三甲基溴化铵 (CTABr)、十六烷基三丙基溴化铵 (CTPABr) 和四正丁基溴化铵 (TBABr)。甲基萘-2-磺酸盐 (β-MeONs)，其 6-磺酸盐衍生物 (β-MeONsS-) 作为 2,6-lutidinium 盐和甲基-5-N,N,N,三甲基萘-1-磺酸铵 (α- MeONsNT+) 作为三氟甲磺酸盐与 Br– 在 CH2Cl2 中反应。随着鎓盐浓度的增加，三种底物的一级速率常数 kobs 线性增加且类似。TBABr 的反应比 CTPABr 和 CTABr 的反应更快，三种底物的反应性顺序为：α-MeONsNT+

  DOI：

  10.1002/ejoc.200600144
• 作为产物：
  描述：

  丹磺酰氟 、 sodium methylate 以 甲醇 为溶剂， 反应 0.25h， 生成 methyl 5-(dimethylamino)naphthalene-1-sulfonate
  参考文献：
  名称：

  Effect of prolonged exposure to organic solvents on the active site environment of subtilisin Carlsberg

  摘要：

  The potential of enzyme catalysis as a tool for organic synthesis is nowadays indisputable, as is the fact that organic solvents affect an enzyme's activity, selectivity and stability. Moreover, it was recently realized that an enzyme's initial activity is substantially decreased after prolonged exposure to organic media, an effect that further hampers their potential as catalysts for organic synthesis. Regrettably, the mechanistic reasons for these effects are still debatable. In the present study we have made an attempt to explain the reasons behind the partial loss of enzyme activity on prolonged exposure to organic solvents. Fluorescence spectroscopic studies of the serine protease subtilisin Carlsberg chemically modified with polyethylene glycol (PEG-SC) and inhibited with a dansyl fluorophore, and dissolved in two organic solvents (acetonitrile and 1,4-dioxane) indicate that when the enzyme is initially introduced into these solvents, the active site environment is similar to that in water: however prolonged exposure to the organic medium causes this environment to resemble that of the solvent in which the enzyme is dissolved. Furthermore, kinetic studies show a reduction on both 14,,,,x and Km as a result of prolonged exposure to the solvents. One interpretation of these results is that during this prolonged exposure to organic solvents the active-site fluorescent label inhibitor adopts a different binding conformation. Extrapolating this to an enzymatic reaction we argue that substrates bind in a less catalytically favorable conformation after the enzyme has been exposed to organic media for several hours. Published by Elsevier B.V.

  DOI：

  10.1016/j.molcatb.2010.01.021

文献信息

• Thiophene-2-carboximidamide Based Selective Neuronal Nitric Oxide Inhibitors
  申请人：Silverman Richard B.

  公开号：US20140066635A1

  公开（公告）日：2014-03-06

  Selective neuronal nitric oxide synthase (nNOS) inhibitor compounds designed with one or more thiophene-2-carboximidamide substituents for improved bioavailability.

  选择性神经型一氧化氮合酶（nNOS）抑制剂化合物设计为具有一个或多个噻吩-2-羧酰胺取代基，以提高生物利用度。
• Combinatorial Dansyl Library and its Applications to pH-Responsive Probes
  作者：Seong Cheol Hong、Dhiraj P. Murale、Jun-Seok Lee

  DOI：10.2174/1386207319666160408150203

  日期：2016.5.10

  properties of the probes, we analyzed their optical properties and chemical yields, with an average of 49 %. The molecules were examined for their pH responses, and DS-2 and DS-45 showed blue-shifts, whereas DS-7 and DS-40 showed red-shifts in wavelength with increasing pH. Finally, cell permeability was investigated by treating SNU-2292 cells. Our results demonstrate the potential application of this library

  在这里，我们报告第一个48成员，基于dansyl的组合荧光库。从探针的电子和结构性质，我们分析了它们的光学性质和化学产率，平均为49％。检查分子的pH响应，并且DS-2和DS-45显示出蓝移，而DS-7和DS-40显示出随pH增加的波长红移。最后，通过处理SNU-2292细胞来研究细胞通透性。我们的结果证明了该文库在生物传感器，生物成像和pH指示剂中的潜在应用。
• Reductively-labile sulfonate ester protecting groups that are rapidly cleaved by physiological glutathione
  作者：Adam Choi、Stephen C. Miller

  DOI：10.1039/c7ob00063d

  日期：——

  Sulfonates are frequently used to endow water solubility on hydrophobic molecules, but the repertoire of sulfonate protecting groups remains limited. Here we describe the first sulfonate esters that can be unmasked by the mild reducing conditions found in live mammalian cells. Self-immolative cleavage releases the sulfonate and the two-electron reduction product of a thioquinone methide.

  磺酸盐经常用于赋予疏水性分子以水溶性，但磺酸盐保护基的种类仍然有限。在这里，我们描述了第一种磺酸酯，它可以被活的哺乳动物细胞中的轻度还原条件所掩盖。自焚的裂解释放出磺酸盐和噻吩甲基化物的二电子还原产物。
• Rate and Product Studies of 5-Dimethylamino-Naphthalene-1-Sulfonyl Chloride under Solvolytic Conditions
  作者：Han Joong Koh、Suk Jin Kang

  DOI：10.5012/bkcs.2014.35.8.2285

  日期：2014.8.20

  The solvolysis rate constants of 5-dimethylamino-naphthalene-1-sulfonyl chloride ((CH3)2NC10H6SO2Cl, 1) in 31 different solvents are well correlated with the extended Grunwald-Winstein equation, using the NT solvent nucleophilicity scale and YCl solvent ionizing scale with sensitivity values of 0.96 ± 0.09 and 0.53 ± 0.03 for l and m, respectively; the correlation coefficient value was 0.955. These

  5-二甲氨基-萘-1-磺酰氯 ((CH3)2NC10H6SO2Cl, 1) 在 31 种不同溶剂中的溶剂分解速率常数与扩展的 Grunwald-Winstein 方程密切相关，使用 NT 溶剂亲核性标度和 YCl 溶剂电离标度l 和 m 的灵敏度值分别为 0.96 ± 0.09 和 0.53 ± 0.03；相关系数值为0.955。可以认为这些 l 和 m 值支持具有类似于苯磺酰氯反应的过渡态 (TS) 结构的 SN2 反应途径。这种解释得到了激活参数的进一步支持，即相对较小的正ΔH≠（12.0至15.9 kcal·mol·1）和较大的负ΔS≠（·23.1至≤36.3 cal·mol·1·K·1）值，和溶剂动力学同位素效应（SKIE，1.34 至 1.88）。还，
• PROTEASOME INHIBITORS
  申请人：Macherla Venkat Rami Reddy

  公开号：US20090298906A1

  公开（公告）日：2009-12-03

  Disclosed herein are compounds of Formula (I) that include a sulfonate ester, ester or ether group. Compounds of Formula (I) can be included in pharmaceutical compositions, and can be used to treating and/or ameliorating a disease or condition, such as cancer, a microbial disease and/or inflammation.

  本文披露了包含磺酸酯、酯或醚基团的化合物(I)。化合物(I)可以包含在药物组合物中，并可用于治疗和/或改善疾病或症状，如癌症、微生物疾病和/或炎症。