N,N-bis(6-methyl-2-picolyl)-p-tolylsulfonamide | 790235-48-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N,N-bis(6-methyl-2-picolyl)-p-tolylsulfonamide
• 英文别名: N,N-di(6-methyl-2-picolyl)-p-tolylsulfonamide；4-methyl-N,N-bis[(6-methylpyridin-2-yl)methyl]benzenesulfonamide
• CAS: 790235-48-2
• 化学式: C₂₁H₂₃N₃O₂S
• 分子量: 381.499
• InChiKey: SLAJSVGBCRGWKY-UHFFFAOYSA-N

物化性质

• 沸点：
  542.9±60.0 °C(Predicted)
• 密度：
  1.224±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  71.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N,N-bis(6-methyl-2-picolyl)-p-tolylsulfonamide 在 硫酸 作用下， 反应 2.0h， 以0.64 g的产率得到bis(6-methyl-2-pyridylmethyl)amine
  参考文献：
  名称：

  Selective Zinc Sensor Molecules with Various Affinities for Zn²⁺, Revealing Dynamics and Regional Distribution of Synaptically Released Zn²⁺ in Hippocampal Slices

  摘要：

  We have developed a series of fluorescent Zn2+ sensor molecules with distinct affinities for Zn2+, because biological Zn2+ concentrations vary over a wide range from sub-nanomolar to millimolar. The new sensors have Kd values in the range of 10(-8)-10(-4) M, compared with 2.7 nM for ZnAF-2. They do not fluoresce in the presence of other biologically important metal ions such as calcium or magnesium, and they can detect Zn2+ within 100 ms. In cultured cells, the fluorescence intensity of ZnAF-2 was saturated at low Zn2+ concentration, while that of ZnAF-3 (K-d = 0.79 mu M) was not saturated even at relatively high Zn2+ concentrations. In hippocampal slices, we measured synaptic release of Zn2+ in response to high-potassium-induced depolarization. ZnAF-2 showed similar levels of fluorescence increase in dentate gyrus (DG), CA3 and CA1, which were indistinguishable. However, ZnAF-3 showed a fluorescence increase only in DG. Thus, by using a combination of sensor molecules, it was demonstrated for the first time that a higher Zn2+ concentration is released in DG than in CA3 or CA1 and that we can easily visualize Zn2+ concentration over a wide range. We believe that the use of various combinations of ZnAF family members will offer unprecedented versatility for fluorescence-microscopic imaging of Zn2+ in biological applications.

  DOI：

  10.1021/ja050301e
• 作为产物：
  描述：

  6-甲基-2-吡啶基甲醇 在 氯化亚砜 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成 N,N-bis(6-methyl-2-picolyl)-p-tolylsulfonamide
  参考文献：
  名称：

  Selective Zinc Sensor Molecules with Various Affinities for Zn²⁺, Revealing Dynamics and Regional Distribution of Synaptically Released Zn²⁺ in Hippocampal Slices

  摘要：

  We have developed a series of fluorescent Zn2+ sensor molecules with distinct affinities for Zn2+, because biological Zn2+ concentrations vary over a wide range from sub-nanomolar to millimolar. The new sensors have Kd values in the range of 10(-8)-10(-4) M, compared with 2.7 nM for ZnAF-2. They do not fluoresce in the presence of other biologically important metal ions such as calcium or magnesium, and they can detect Zn2+ within 100 ms. In cultured cells, the fluorescence intensity of ZnAF-2 was saturated at low Zn2+ concentration, while that of ZnAF-3 (K-d = 0.79 mu M) was not saturated even at relatively high Zn2+ concentrations. In hippocampal slices, we measured synaptic release of Zn2+ in response to high-potassium-induced depolarization. ZnAF-2 showed similar levels of fluorescence increase in dentate gyrus (DG), CA3 and CA1, which were indistinguishable. However, ZnAF-3 showed a fluorescence increase only in DG. Thus, by using a combination of sensor molecules, it was demonstrated for the first time that a higher Zn2+ concentration is released in DG than in CA3 or CA1 and that we can easily visualize Zn2+ concentration over a wide range. We believe that the use of various combinations of ZnAF family members will offer unprecedented versatility for fluorescence-microscopic imaging of Zn2+ in biological applications.

  DOI：

  10.1021/ja050301e

文献信息

• Linear Bidentate Ligands (L) with Two Terminal Pyridyl N-Donor Groups Forming Pt(II)LCl₂ Complexes with Rare Eight-Membered Chelate Rings
  作者：Kokila Ranasinghe、Patricia A. Marzilli、Svetlana Pakhomova、Luigi G. Marzilli

  DOI：10.1021/acs.inorgchem.8b01943

  日期：2018.10.15

  5′-Me4dpa)Cl2 complexes undergo monosolvolysis in DMSO-d6 to form the [Pt(N(SO2R)3,3′,5,5′-Me4dpa)(DMSO-d6)Cl]+ cations. However, unlike typical cis-PtLCl2 complexes, the Pt(N(SO2R)3,3′,5,5′-Me4dpa)Cl2 complexes surprisingly do not react readily with the excellent N-donor bioligand guanosine. A comparison of the structural features of over 50 known relevant Pt(II) complexes having smaller chelate rings with

  NMR和X射线衍射研究是在用新的N供体配体N（SO 2 R）Me n dpa（R = Me，Tol; n = 2，4）制备的Pt（II）LCl 2络合物上进行的。这些配体不同于N（H）dpa（di-2-picolylamine），其中心N在叔磺酰胺基而不是仲胺基内，而Me在6,6'-位（n = 2）或吡啶环的3,3'，5,5'-位（n = 4）。所述Ñ（SO 2 R）3,3'，5,5'--ME 4个DPA配体在铂（二齿配位方式Ñ（SO 2 R）3,3'，5,5'--ME4 dpa）Cl 2络合物，形成稀有的八元螯合环。磺酰胺N原子不与Pt（II）结合，这与文献中的指示一致，即叔磺酰胺不太可能在配位溶剂的溶液中锚定两个子午配位的五元螯合环。所述Ñ（SO 2 R）-6,6'--ME 2 DPA配体的单齿的方式坐标，以形成双核配合物[反式-Pt（DMSO）氯2 ] 2（Ñ（SO 2 R）-6,6'-二我2
• New fac-[ReI(CO)3(Ltri)]Y complexes of linear N,N′,N′′-tridentate ligands (Ltri) with terminal imidazolyl or pyridyl ring (N and N′′) and central tertiary sulfonamide (N′) N-donors. Effects of size and substituents of the terminal N-donor rings and the rarely found direct sulfonamide N to metal bond
  作者：Kokila Ranasinghe、Patricia A. Marzilli、Svetlana Pakhomova、Luigi G. Marzilli

  DOI：10.1016/j.ica.2021.120781

  日期：2022.4

  groups projecting toward the coordination sphere, while the Ltri = N(SO2R)1,1′-Me2dma and N(SO2R)3,3′,5,5′-Me4dpa complexes are indefinitely robust in solution. In contrast to the similar behavior of fac-[Re(CO)3Ltri]Y complexes for Ltri = N(SO2R)1,1′-Me2dma and N(SO2R)3,3′,5,5′-Me4dpa, only the latter dissociates over time in DMSO‑d6 for [Pt(“Ltri”)Cl2] complexes (unpublished), where the sulfonamide N in

  fac -[Re(CO) 3 L tri ]Y (Y = ClO 4 -或 PF 6 - ) 配合物用N , N' , N'' -供体三齿配体 (L tri ), N (SO 2 R) 制备1,1 '- Me 2 dma 和N (SO 2 R)Me n dpa (R = Me 或 Tol)。这两个新的Ñ（SO 2 R）1,1 ' -我2 DMA的配体是母体配体的衍生物，Ñ（H）1,1- ' -Me2 dma（双（1-甲基-2-甲基咪唑基）胺），其中心 N 位于叔磺酰胺基团内，而不是仲胺基团。除了具有叔磺酰胺基团之外，N (SO 2 R)Me n dpa 配体与母体配体N (H)dpa (2-甲基吡啶胺) 的不同之处在于，在 6,6 ' - (n = 2) 或 3,3 ' ,5,5 ' - (n = 4) 吡啶环的位置。L tri与正常长度的 Re-N '（磺酰胺 N）键在表面上配位。只有 L
• US7696245B2
  申请人：——

  公开号：US7696245B2

  公开（公告）日：2010-04-13
• Selective Zinc Sensor Molecules with Various Affinities for Zn²⁺, Revealing Dynamics and Regional Distribution of Synaptically Released Zn²⁺ in Hippocampal Slices
  作者：Kensuke Komatsu、Kazuya Kikuchi、Hirotatsu Kojima、Yasuteru Urano、Tetsuo Nagano

  DOI：10.1021/ja050301e

  日期：2005.7.1

  We have developed a series of fluorescent Zn2+ sensor molecules with distinct affinities for Zn2+, because biological Zn2+ concentrations vary over a wide range from sub-nanomolar to millimolar. The new sensors have Kd values in the range of 10(-8)-10(-4) M, compared with 2.7 nM for ZnAF-2. They do not fluoresce in the presence of other biologically important metal ions such as calcium or magnesium, and they can detect Zn2+ within 100 ms. In cultured cells, the fluorescence intensity of ZnAF-2 was saturated at low Zn2+ concentration, while that of ZnAF-3 (K-d = 0.79 mu M) was not saturated even at relatively high Zn2+ concentrations. In hippocampal slices, we measured synaptic release of Zn2+ in response to high-potassium-induced depolarization. ZnAF-2 showed similar levels of fluorescence increase in dentate gyrus (DG), CA3 and CA1, which were indistinguishable. However, ZnAF-3 showed a fluorescence increase only in DG. Thus, by using a combination of sensor molecules, it was demonstrated for the first time that a higher Zn2+ concentration is released in DG than in CA3 or CA1 and that we can easily visualize Zn2+ concentration over a wide range. We believe that the use of various combinations of ZnAF family members will offer unprecedented versatility for fluorescence-microscopic imaging of Zn2+ in biological applications.