3.3-Dichlor-<3.3'-azo-n-pentan> | 53651-84-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3.3-Dichlor-<3.3'-azo-n-pentan>
• 英文别名: Azobis-3-chlor-3-pentan；azodi(1-chloro-1-ethylpropane)；bis-(1-chloro-1-ethyl-propyl)-diazene；3,3'-dichloro-[3,3']azopentane；3,3'-Dichlor-[3,3']azopentan；Bis(3-chloropentan-3-yl)diazene
• CAS: 53651-84-6
• 化学式: C₁₀H₂₀Cl₂N₂
• 分子量: 239.188
• InChiKey: PHUYKIJIHYSLAD-UHFFFAOYSA-N

物化性质

• 熔点：
  0 °C
• 沸点：
  236.9±25.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  24.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3.3-Dichlor-<3.3'-azo-n-pentan> 、 1-(4-甲基哌嗪)乙腈 在 氯化锑(V) 作用下， 以 二氯甲烷 为溶剂， 反应 2.17h， 以70%的产率得到1-[(1,5-diethyl-1H-1,2,4-triazol-3-yl)methyl]-4-methylpiperazine
  参考文献：
  名称：

  DNA-directed alkylating agents: synthesis, antitumor activity and DNA affinity of bis-N,N′-trisubstituted 1,2,4-triazolo-piperazines

  摘要：

  A series of 1,4-bis-(1,5-dialkyl-1H-1,2,4-triazol-ylmethyl)piperazines and N-methyl-piperazine analogs were prepared spontaneously from the cycloaddition of various reactive cumulenes with the piperazino-1,4-(bis-ethanenitrile) and 1-cyanomethyl-4-methyl-piperazine, respectively. The new compounds were evaluated for their DNA affinity and antitumor activity.

  DOI：

  10.1016/j.farmac.2003.08.006
• 作为产物：
  描述：

  diethyl ketone azine 在 氯 、 Petroleum ether 作用下， 生成 3.3-Dichlor-<3.3'-azo-n-pentan>
  参考文献：
  名称：

  Benzing,E., Justus Liebigs Annalen der Chemie, 1960, vol. 631, p. 1 - 9

  摘要：

  DOI：

文献信息

• Synthesis, Structure, and <i>In Vitro</i> Anti-HIV Activity of New Pyrazole, 1,2,4-Thiadiazole, and 1,2,4-Triazole Derivatives
  作者：Y. A. Al-Soud

  DOI：10.1080/10426500801968003

  日期：2008.9.15

  α,α′-Dichloroazo compounds 6 react with Lewis acid to furnish 1-(chloroalkyl)-1-aza-2-azoniaallene salts 4. The cations 4 react with acetylenes, isothiocyanates, isocyanates, and carbodiimides under [3+2]-cycloaddition. The cycloadducts undergo consecutive reactions, e.g., [1,2]-shifts of alkyl groups. The newly synthesized products were evaluated for their anti-HIV-1 and anti-HIV-2 activity in MT-4

  α,α'-二氯偶氮化合物 6 与路易斯酸反应生成 1-(氯代烷基)-1-氮杂-2-氮杂丙二烯盐 4。阳离子 4 与乙炔、异硫氰酸酯、异氰酸酯和碳二亚胺在 [3+2]- 下反应环加成。环加合物经历连续反应，例如烷基的[1,2]-移位。评估了新合成的产品在 MT-4 细胞中的抗 HIV-1 和抗 HIV-2 活性。
• New Substituted Thiazol-2-ylidene-benzamides and Their Reaction with 1-Aza-2-azoniaallene Salts. Synthesis and anti-HIV Activity
  作者：Aamer Saeed、Najim A. Al-Masoudi、Amjed A. Ahmed、Christophe Pannecouque

  DOI：10.1515/znb-2011-0512

  日期：2011.5.1

  A series of N-(3-(substituted-alkyl- or halophenyl)-4-methylthiazol-2(3H)-ylidene)-substituted alkyl- or halo-benzamides 21 - 40 were prepared by base-catalyzed cyclization of the corresponding 1-(substituted-alkyl- or halo-benzoyl)-3-(substituted-halophenyl)thioureas 1 - 20. Substituted pyrazolo[ 4,3-d]thiazol-5(6aH)-ylidene)benzamides 45a - d were synthesized by cycloaddition of compound 45 with the reactive cumulene intermediates 42a - d. All compounds were evaluated for their antiviral activity against the replication of HIV^-1 and HIV-2 in MT-4. Compounds 35 and 39 showed an IC₅₀ of 2.02 μgmL⁻¹ and 0.40 μgmL⁻¹ against the HIV-2 strain ROD with CC₅₀ of ≥ 104.00 μgmL⁻¹ and > 125.00 μgmL⁻¹, respectively, resulting in a selectivity index of ≥ 52 and > 313. Based on the chemical structure of compounds 35 and 39, these molecules can be proposed to act as NNRTIs. However, it is exceptional to observe an antiretroviral activity that is limited to HIV-2

  一系列N-(3-(取代烷基或卤代苯基)-4-甲基噻唑-2(3H)-基)-取代烷基或卤代苯甲酰胺21-40通过对应的1-(取代烷基或卤代苯甲酰)-3-(取代卤代苯基)硫脲1-20的碱催化环化反应制备。通过将化合物45与反应性累烯中间体42a-d进行环加成反应合成了取代吡唑并[4,3-d]噻唑-5(6aH)-基)苯甲酰胺45a-d。评估所有化合物对MT-4中HIV-1和HIV-2的复制的抗病毒活性。化合物35和39对HIV-2 ROD株显示了IC50值分别为2.02 μg/mL和0.40 μg/mL，CC50值分别为≥104.00 μg/mL和>125.00 μg/mL，因此选择性指数分别为≥52和>313。根据化合物35和39的化学结构，这些分子可能作为非核苷逆转录酶抑制剂。然而，观察到限于HIV-2的抗逆转录病毒活性是异常的。
• Duismann,W. et al., Justus Liebigs Annalen der Chemie, 1974, p. 1348 - 1356
  作者：Duismann,W. et al.

  DOI：——

  日期：——
• Synthesis and Antiviral Activity of 1,5-and 1,3-Dialkyl-1,2,4-triazole<i>C</i>-Nucleosides Derived from 1-(Chloroalkyl)-1-aza-2-azoniaallene Salts
  作者：Yaseen A. Al-soud、Wasfi A. Al-masoudi、Rajab Abu El-halawa、Najim Al-masoudi

  DOI：10.1080/07328319908044859

  日期：1999.9

  Reactions of alpha,alpha'-dichloroazo compounds 2 with SbCl5 gave 1-(chloroalkyl)-1-aza-2-azoniaallene salts 3 as reactive intermediates. Cycloadditions of 3 with the ribofuranosyl cyanide 4 afforded the beta-D-ribofuranosyl-1,2,4-triazolium salts 5, which rearranged spontaneously to salts 6. Hydrolysis of 6 gave the 1,2,4-triazole C-nucleosides 7, which yielded the free nucleosides 8 after deblocking. Analogously, 12 was prepared from the cycloaddition of 4 with the alpha-chloroazo compound 10 in the presence of SbCl5. Deblocking of 12 with sodium methoxide afforded 13. Compounds 8a,b,e,f and 13 were tested against HIV-1, HIV-2, HSV-1 and HSV-2 and were found to be inactive.
• Synthesis of new 1H-1,2,4-triazolylcoumarins and their antitumor and anti-HIV activities
  作者：Y. A. Al-Soud、I. A. Al-Masoudi、B. Saeed、U. Beifuß、N. A. Al-Masoudi

  DOI：10.1007/s10593-006-0130-2

  日期：2006.5