1,4-bis(chloromethoxy)crotonylene | 138649-02-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,4-bis(chloromethoxy)crotonylene
• 英文别名: 1,4-bis-chloromethoxy-but-2-yne；1,4-Bis-chlormethoxy-but-2-in；Butin-(2)-diol-(1.4)-bis-chlormethylaether；1,4-bis(chloromethoxy)but-2-yne
• CAS: 138649-02-2
• 化学式: C₆H₈Cl₂O₂
• 分子量: 183.034
• InChiKey: MNESZOKJVAILOB-UHFFFAOYSA-N

物化性质

• 沸点：
  122-124 °C(Press: 12 Torr)
• 密度：
  1.266 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  1.42
• 重原子数：
  10.0
• 可旋转键数：
  4.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1,4-bis(chloromethoxy)crotonylene 、 sodium butanolate 在 正丁醇 作用下， 生成 1,4-bis-butoxymethoxy-but-2-yne
  参考文献：
  名称：

  Arbusow; Winokurowa, Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1953, p. 829,835;engl.Ausg.S.735,739

  摘要：

  DOI：
• 作为产物：
  描述：

  三聚甲醛 、 丁炔二醇 在 盐酸 作用下， 生成 1,4-bis(chloromethoxy)crotonylene
  参考文献：
  名称：

  Trinitroethyl ethers of substituted alcohols

  摘要：

  The influence of the trinitromethane salt cations and the substituents in the alkyl moiety of chloromethyl ethers of alcohols on the yields of trinitroethyl ethers of the substituted alcohols formed from them was established. On this basis a representative series of previously unavailable trinitroethanol ethers was synthesized.

  DOI：

  10.1007/bf00961040

文献信息

• Design, synthesis and biological characterization of novel inhibitors of CD38
  作者：Min Dong、Yuan-Qi Si、Shuang-Yong Sun、Xiao-Ping Pu、Zhen-Jun Yang、Liang-Ren Zhang、Li-He Zhang、Fung Ping Leung、Connie Mo Ching. Lam、Anna Ka Yee Kwong、Jianbo Yue、Yeyun Zhou、Irina A. Kriksunov、Quan Hao、Hon Cheung Lee

  DOI：10.1039/c0ob00768d

  日期：——

  Human CD38 is a novel multi-functional protein that acts not only as an antigen for B-lymphocyte activation, but also as an enzyme catalyzing the synthesis of a Ca2+ messenger molecule, cyclic ADP-ribose, from NAD+. It is well established that this novel Ca2+ signaling enzyme is responsible for regulating a wide range of physiological functions. Based on the crystal structure of the CD38/NAD+ complex, we synthesized a series of simplified N-substituted nicotinamide derivatives (Compound1–14). A number of these compounds exhibited moderate inhibition of the NAD+ utilizing activity of CD38, with Compound4 showing the highest potency. The crystal structure of CD38/Compound4 complex and computer simulation of Compound7 docking to CD38 show a significant role of the nicotinamide moiety and the distal aromatic group of the compounds for substrate recognition by the active site of CD38. Biologically, we showed that both Compounds4 and 7 effectively relaxed the agonist-induced contraction of muscle preparations from rats and guinea pigs. This study is a rational design of inhibitors for CD38 that exhibit important physiological effects, and can serve as a model for future drug development.

  人类CD38是一种新型多功能蛋白，不仅作为B淋巴细胞激活的抗原，同时也是一种酶，催化从NAD+合成钙离子信使分子环状ADP-核糖。已知这一新型钙信号酶在调节广泛生理功能方面起着重要作用。基于CD38/NAD+复合物的晶体结构，我们合成了一系列简化的N取代烟酰胺衍生物（化合物1–14）。其中一些化合物对CD38的NAD+利用活性表现出中等抑制作用，化合物4显示出最高的效力。CD38/化合物4复合物的晶体结构及化合物7与CD38对接的计算机模拟显示，在底物被CD38活性位点识别的过程中，烟酰胺部分和化合物的远端芳香基团发挥了重要作用。在生物学上，我们展示了化合物4和7能够有效放松来自大鼠和豚鼠肉体准备的激动剂诱导收缩。本研究是对CD38抑制剂的合理设计，展现了重要的生理效应，并可作为未来药物开发的模型。
• Synthesis and evaluation of novel bis-pyridinium oximes as reactivators of DFP-inhibited acetylcholinesterase
  作者：Jyotiranjan Acharya、Arvind Kumar Gupta、Devendra Kumar Dubey、Syed Kalbey Raza

  DOI：10.1016/j.ejmech.2008.02.029

  日期：2009.3

  4-bis-methoxymethyl but-2-yne linkers were synthesized and their in vitro reactivation efficacy was evaluated against diisopropyl phosphorofluoridate (DFP) inhibited acetylcholinesterase (AChE) and compared with the established antidote 2-PAM and obidoxime. However, the best reactivation was observed with the standard oxime 2-PAM. The reactivation efficacy of 1,3-dimethoxymethyl benzene bis-[4,4′-(hydroxyiminomethyl)

  合成了一系列由双-甲氧基甲基苯，1,4-双-甲氧基甲基（顺式）-丁-2-烯和1,4-双-甲氧基甲基丁-2-炔连接基连接的新型双吡啶肟。评估了对氟磷酸二异丙酯（DFP）抑制的乙酰胆碱酯酶（AChE）的体外再激活功效，并将其与已建立的解毒剂2-PAM和Obidoxime进行了比较。但是，使用标准肟2-PAM可以观察到最佳的再活化。1,3-二甲氧基甲基苯双-[4,4'-（羟基亚氨基甲基）吡啶鎓]二氯化物（3d）和1,4-二甲氧基丁-2-烯双-[4,4'-（羟基亚氨基甲基）吡啶鎓的活化活性]二氯化物（3克）与另一种标准解毒剂奥比多肟相当。
• Lefebvre; Dupont; Dulou, Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1949, vol. 229, p. 223
  作者：Lefebvre、Dupont、Dulou

  DOI：——

  日期：——