(3-azido-5-iodo)benzyl bromide | 528893-95-0

• 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: (3-azido-5-iodo)benzyl bromide
• 英文别名: 1-Azido-3-(bromomethyl)-5-iodobenzene
• CAS: 528893-95-0
• 化学式: C₇H₅BrIN₃
• 分子量: 337.945
• InChiKey: BEOSKQGCYVMZFN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  14.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  dantrolene sodium 、 (3-azido-5-iodo)benzyl bromide 以 N,N-二甲基甲酰胺 为溶剂， 反应 14.5h， 以85%的产率得到3-[(3-azido-5-iodophenyl)methyl]-1-[(E)-[5-(4-nitrophenyl)furan-2-yl]methylideneamino]imidazolidine-2,4-dione
  参考文献：
  名称：

  [125I]-N-[(3-Azido-5-iodo)benzyl]dantrolene and [125I]-N-{[3-Iodo-5-(3-trifluoromethyl-3H-diazirin-3-yl)]benzyl}dantrolene: photoaffinity probes specific for the physiological Ca2+ release from sarcoplasmic reticulum of skeletal muscle

  摘要：

  In order to capture and identify key molecules that regulate the release of Ca2+ from the sarcoplasmic reticulum (SR) of skeletal muscle, we designed specific photoaffinity probes based on the structural modification of dantrolene. Thus, GIF-0082 and GIF-0276 possessing azido- and trifluoromethyldiazirinyl-benzyl groups, respectively, at the hydantoin moiety were found to have a highly selective inhibitory effect on physiological Ca2+ release (PCR) without affecting Ca2+-induced Ca2+ release (CICR). Successful realization of the sharp discrimination between PCR and CICR has led to the creation of [I-125]GIF-0082 and [I-125]GIF-0276, which were synthesized by substituting a stannyl group with I-125 in the corresponding phenylstannane precursors. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(02)00701-1
• 作为产物：
  描述：

  3-iodo-5-nitrobenzyl alcohol 在 四溴化碳 、 溶剂黄146 、 三苯基膦 、 tin(ll) chloride 、 sodium nitrite 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 4.75h， 生成 (3-azido-5-iodo)benzyl bromide
  参考文献：
  名称：

  [125I]-N-[(3-Azido-5-iodo)benzyl]dantrolene and [125I]-N-{[3-Iodo-5-(3-trifluoromethyl-3H-diazirin-3-yl)]benzyl}dantrolene: photoaffinity probes specific for the physiological Ca2+ release from sarcoplasmic reticulum of skeletal muscle

  摘要：

  In order to capture and identify key molecules that regulate the release of Ca2+ from the sarcoplasmic reticulum (SR) of skeletal muscle, we designed specific photoaffinity probes based on the structural modification of dantrolene. Thus, GIF-0082 and GIF-0276 possessing azido- and trifluoromethyldiazirinyl-benzyl groups, respectively, at the hydantoin moiety were found to have a highly selective inhibitory effect on physiological Ca2+ release (PCR) without affecting Ca2+-induced Ca2+ release (CICR). Successful realization of the sharp discrimination between PCR and CICR has led to the creation of [I-125]GIF-0082 and [I-125]GIF-0276, which were synthesized by substituting a stannyl group with I-125 in the corresponding phenylstannane precursors. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(02)00701-1

文献信息

• Effects of dantrolene and its derivatives on Ca²⁺ release from the sarcoplasmic reticulum of mouse skeletal muscle fibres
  作者：Takaaki Ikemoto、Takamitsu Hosoya、Hiroshi Aoyama、Yasutaka Kihara、Masaaki Suzuki、Makoto Endo

  DOI：10.1038/sj.bjp.0704307

  日期：2001.10

  We analysed the effect of dantrolene (Dan) and five newly synthesized derivatives (GIFs) on Ca2+ release from the sarcoplasmic reticulum (SR) of mouse skeletal muscle. In intact muscles, GIF‐0185 reduced the size of twitch contraction induced by electrical stimulation to the same extent as Dan. GIF‐0082, an azido‐functionalized Dan derivative, also inhibited twitch contraction, although the extent of inhibition was less than that of Dan and of GIF‐0185. In skinned fibres, Dan inhibited Ca2+‐induced Ca2+ release (CICR) under Mg2+‐free conditions at room temperature. In contrast, GIF‐0082 and GIF‐0185 showed no inhibitory effect on CICR under the same conditions. Dan‐induced inhibition of CICR was not affected by the presence of GIF‐0082, whereas it was diminished in the presence of GIF‐0185. GIF‐0082 and GIF‐0185 significantly inhibited clofibric acid (Clof)‐induced Ca2+ release, as did Dan. Several Dan derivatives other than GIF‐0082 and GIF‐0185 showed an inhibitory effect on twitch tension but not on the CICR mechanism. All of these derivatives inhibited Clof‐induced Ca2+ release. The magnitudes of inhibition of Clof‐induced Ca2+ release by all Dan derivatives were well correlated with those of twitch inhibition. This supports the notion that the mode of Clof‐induced opening of the RyR‐Ca2+ release channel may be similar to that of physiological Ca2+ release (PCR). These results indicate that the difference in opening modes of the RyR‐Ca2+ release channel is recognized by certain Dan derivatives. British Journal of Pharmacology (2001) 134, 729–736; doi:10.1038/sj.bjp.0704307

  我们分析了丹特罗伦（Dan）及其五种新合成的衍生物（GIFs）对小鼠骨骼肌肌质网（SR）中钙离子（Ca²+）释放的作用。
  在完整肌肉中，GIF-0185将电刺激诱导的 twitch 收缩幅度降低至与 Dan 相同的程度。另一种叠氮功能化的 Dan 衍生物 GIF-0082也抑制了 twitch 收缩，尽管其抑制程度低于 Dan 和 GIF-0185。
  在去膜肌纤维中，Dan 在无 Mg²+ 的室温条件下抑制钙诱导的钙释放（CICR）。与此相反，GIF-0082 和 GIF-0185 在相同条件下对 CICR 没有抑制作用。
  Dan 对 CICR 的抑制作用不受 GIF-0082 的存在影响，但在 GIF-0185 存在时被减弱。
  GIF-0082 和 GIF-0185 显著抑制了氯芬酸（Clof）诱导的 Ca²+ 释放，与 Dan 作用相同。
  除 GIF-0082 和 GIF-0185 外，其他几种 Dan 衍生物也抑制 twitch 张力，但不影响 CICR 机制。所有这些衍生物均抑制 Clof 诱导的 Ca²+ 释放。
  所有 Dan 衍生物对 Clof 诱导的 Ca²+ 释放的抑制作用程度与对 twitch 的抑制作用程度密切相关。这支持了 Clof 诱导的 RyR-Ca²+ 释放通道开启模式可能与生理状态下 Ca²+ 释放（PCR）相似的观点。
  这些结果表明，某些 Dan 衍生物能够识别 RyR-Ca²+ 释放通道开启模式的差异。
  *《英国药理学杂志》（2001）134卷，729–736页；doi:10.1038/sj.bjp.0704307