4-dipropylamino-N-methyl-3,5-dinitrobenzenesulfonamide | 19044-89-4

• 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: 4-dipropylamino-N-methyl-3,5-dinitrobenzenesulfonamide
• 英文别名: N1-methyl-3,5-dinitro-N4,N4-dipropylsulfanilamide；Benzenesulfonamide, 4-(dipropylamino)-N-methyl-3,5-dinitro-；4-(dipropylamino)-N-methyl-3,5-dinitrobenzenesulfonamide
• CAS: 19044-89-4
• 化学式: C₁₃H₂₀N₄O₆S
• 分子量: 360.391
• InChiKey: SIQXMYBLKQFLEV-UHFFFAOYSA-N

物化性质

• 熔点：
  145-146 °C
• 沸点：
  496.5±55.0 °C(Predicted)
• 密度：
  1.346±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  149
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-dipropylamino-N-methyl-3,5-dinitrobenzenesulfonamide 、 氯甲酸丁酯 在 potassium carbonate 作用下， 以 乙二醇二甲醚 为溶剂， 生成 N1-butoxycarbonyl-N1-methyl-3,5-dinitro-N4,N4-di-n-propylsulfanilamide
  参考文献：
  名称：

  Herbicidal N.sup.1 -methoxycarbonyl-N.sup.1 -alkyl-3,5-dinitro-N.sup.4

  摘要：

  N.sup.1-甲氧羰基-N.sup.1-烷基-3,5-二硝基-N.sup.4,N.sup.4-二烷基磺胺酰胺可作为预防狗尾草的除草剂，在对黑麦草和二叶草等草坪草基本没有除草效果的情况下非常有用。

  公开号：

  US03971650A1
• 作为产物：
  描述：

  potassium 3,5-dinitro-N⁴,N⁴-di-n-propylsulfonate 在 五氯化磷 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 4-dipropylamino-N-methyl-3,5-dinitrobenzenesulfonamide
  参考文献：
  名称：

  Synthesis and Antitubulin Activity of N- and N⁴-Substituted 3,5-Dinitro Sulfanilamides against African Trypanosomes and Leishmania

  摘要：

  Thirty analogues of N-1-phenyl-3,5-dinitro-N-4,N-4-di-n-propylsulfanilamide (GB-II-5, compound 3), a new antikinetoplastid antimitotic agent, have been synthesized and evaluated. The addition of simple functional groups to the N1 aromatic ring generally decreases antiparasitic and antimitotic potency, but placement of a dibutyl substituent at the N4 nitrogen to give N-1-phenyl-3,5-dinitro-N-4,N-4-di-n-butylsulfanilamide (compound 35) augments antitrypanosomal and antileishmanial activity. Compound 35 possesses IC50 values of 0.12 and 2.6 muM against cultured T. brucei and L. donovani amastigote-like forms, surpassing the activity of compound 3 against these parasites by 3.4- and 1.9-fold, respectively. Compound 35 inhibits the assembly of leishmanial tubulin with an IC50 of 6.9 muM and displays antimitotic effects in cultured T brucei as assessed by flow cytometry, but shows little effect on purified mammalian tubulin, and displays 100-fold selectivity for trypanosomes over two mammalian cell lines. Although 3 and 35 were not effective in initial in vivo antitrypanosomal assays, the in vitro potency and ;selectivity of these compounds make N-1-aryl-3,5-dinitro-N-4,N-4-dialkylsulfanilamides a promising new class of antikinetoplastid agents that act on parasite tubulin.

  DOI：

  10.1021/jm0304461

文献信息

• Nematocidal 4-amino-N-thio-substituted 3,5-dinitrobenzenesulfonamides
  申请人：Chevron Research Company

  公开号：US04041159A1

  公开（公告）日：1977-08-09

  Compounds of the formula ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 are alkyl and R.sup.4 is alkyl, haloalkyl or aryl.

  化合物的公式为##STR1##其中R.sup.1，R.sup.2和R.sup.3是烷基，R.sup.4是烷基，卤代烷基或芳基。
• US4041159A
  申请人：——

  公开号：US4041159A

  公开（公告）日：1977-08-09
• Herbicidal N.sup.1 -methoxycarbonyl-N.sup.1 -alkyl-3,5-dinitro-N.sup.4
  申请人：Chevron Research Company

  公开号：US03971650A1

  公开（公告）日：1976-07-27

  N.sup.1 -methoxycarbonyl-N.sup.1 -alkyl-3,5-dinitro-N.sup.4,N.sup.4 -dialkylsulfanilamides are useful as pre-emergence herbicides for crabgrass, with essentially no herbicidal effects on lawn grasses such as ryegrass and dichondra.

  N.sup.1-甲氧羰基-N.sup.1-烷基-3,5-二硝基-N.sup.4,N.sup.4-二烷基磺胺酰胺可作为预防狗尾草的除草剂，在对黑麦草和二叶草等草坪草基本没有除草效果的情况下非常有用。
• Synthesis and Antitubulin Activity of N- and N⁴-Substituted 3,5-Dinitro Sulfanilamides against African Trypanosomes and <i>Leishmania</i>
  作者：Gautam Bhattacharya、Johnathan Herman、Dawn Delfín、Manar M. Salem、Todd Barszcz、Mike Mollet、Guy Riccio、Reto Brun、Karl A. Werbovetz

  DOI：10.1021/jm0304461

  日期：2004.3.1

  Thirty analogues of N-1-phenyl-3,5-dinitro-N-4,N-4-di-n-propylsulfanilamide (GB-II-5, compound 3), a new antikinetoplastid antimitotic agent, have been synthesized and evaluated. The addition of simple functional groups to the N1 aromatic ring generally decreases antiparasitic and antimitotic potency, but placement of a dibutyl substituent at the N4 nitrogen to give N-1-phenyl-3,5-dinitro-N-4,N-4-di-n-butylsulfanilamide (compound 35) augments antitrypanosomal and antileishmanial activity. Compound 35 possesses IC50 values of 0.12 and 2.6 muM against cultured T. brucei and L. donovani amastigote-like forms, surpassing the activity of compound 3 against these parasites by 3.4- and 1.9-fold, respectively. Compound 35 inhibits the assembly of leishmanial tubulin with an IC50 of 6.9 muM and displays antimitotic effects in cultured T brucei as assessed by flow cytometry, but shows little effect on purified mammalian tubulin, and displays 100-fold selectivity for trypanosomes over two mammalian cell lines. Although 3 and 35 were not effective in initial in vivo antitrypanosomal assays, the in vitro potency and ;selectivity of these compounds make N-1-aryl-3,5-dinitro-N-4,N-4-dialkylsulfanilamides a promising new class of antikinetoplastid agents that act on parasite tubulin.