4-硝基-1H-咪唑-5-磺酰氯 | 90521-82-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 4-硝基-1H-咪唑-5-磺酰氯
• 英文名称: 4-chlorosulfonyl-5-nitroimidazole
• 英文别名: 5-nitroimidazole-4-sulfonyl chloride；5(4)-nitro-1H-imidazole-4(5)-sulfonyl chloride；4-Nitro-1h-imidazole-5-sulfonyl chloride；5-nitro-1H-imidazole-4-sulfonyl chloride
• CAS: 90521-82-7
• 化学式: C₃H₂ClN₃O₄S
• mdl: MFCD20617723
• 分子量: 211.586
• InChiKey: LKMKCGWWIZLJAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  117
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  乙胺 、 4-硝基-1H-咪唑-5-磺酰氯 在 盐酸 作用下， 以 水 为溶剂， 反应 72.5h， 以66%的产率得到5-nitro-N-ethyl-1H-imidazole-4-sulfonamide hydrochloride
  参考文献：
  名称：

  [EN] 8 - SULFO - IMIDAZOTETRAZIN- 4 - ONE COMPOUNDS AND THEIR USE AS ANTICANCER DRUG
  [FR] COMPOSÉS 8-SULFO-IMIDAZOTÉTRAZIN-4-ONE ET LEUR UTILISATION EN TANT QUE MÉDICAMENT ANTICANCÉREUX

  摘要：

  提供具有化学式（I）及其药用可接受的盐、水合物或溶剂化合物（I）的其中B、X和Y的定义如本文所述。这些化合物在调节细胞增殖、抑制细胞周期进展和/或促进凋亡的方法中有用，并用于治疗增生性疾病。

  公开号：

  WO2012085501A1
• 作为产物：
  描述：

  4(5)-mercapto-5(4)-nitroimidazole 在 盐酸 、 水 、 氯 作用下， 以66%的产率得到4-硝基-1H-咪唑-5-磺酰氯
  参考文献：
  名称：

  [EN] 8 - SULFO - IMIDAZOTETRAZIN- 4 - ONE COMPOUNDS AND THEIR USE AS ANTICANCER DRUG
  [FR] COMPOSÉS 8-SULFO-IMIDAZOTÉTRAZIN-4-ONE ET LEUR UTILISATION EN TANT QUE MÉDICAMENT ANTICANCÉREUX

  摘要：

  提供具有化学式（I）及其药用可接受的盐、水合物或溶剂化合物（I）的其中B、X和Y的定义如本文所述。这些化合物在调节细胞增殖、抑制细胞周期进展和/或促进凋亡的方法中有用，并用于治疗增生性疾病。

  公开号：

  WO2012085501A1

文献信息

• Synthesis of 5-Amino-4-sulfonamidoimidazole nucleosides as potential inhibitors of purine nucleotide biosynthesis, and of an imidazothiadiazine dioxide analogue of adenosine
  作者：A. Scott Frame、Richard H. Wightman、Grahame Mackenzie

  DOI：10.1016/0040-4020(96)00472-3

  日期：1996.7

  potential inhibitors of the intermediate stages in the pathway for de novo biosynthesis of purine nucleotides. An intermediate in the preparation of 6 could be cyclized to give 9, a novel analogue of adenosine and inosine, and a potential inhibitor of enzymes which effect reactions at C-6 of purine nucleosides or nucleotides.

  已经制备了5-氨基-4-磺酰胺基-1-（β-d-呋喃呋喃糖基）咪唑6和两种或更多种复杂的磺酰胺，其中一种（8）掺入了l-天冬氨酰作为潜在的中间阶段抑制剂。嘌呤核苷酸从头开始生物合成的途径。可以将制备6的中间体环化，得到9，一种腺苷和肌苷的新型类似物，以及一种可能的酶抑制剂，其影响嘌呤核苷或核苷酸在C-6处的反应。
• Synthesis of 5-amino-4-sulfonamidoimidazole nucleosides as potential inhibitors of purine biosynthesis, and of an imidazothiadiazine dioxide analogue of adenosine
  作者：A Scott Frame、Grahame Mackenzie、Richard H. Wightman

  DOI：10.1016/0040-4039(94)85344-4

  日期：1994.10

  5-Amino-4-sulfonamido-1-(β-D-ribofuranosyl)imidazole 5 and two more complex sulfonamides 6 and 7 have been prepared as potential inhibitors of intermediate stages in the de novo biosynthesis of purine nucleotides; cyclization of a protected form of 5 gave 5-(β-D-ribofuranosyl)imidazo[4,5-e]-1,2,4-thiadiazine-1,1-dioxide 8, a novel analogue of adenosine and inosine.

  已经制备了5-氨基-4-磺酰胺基-1-（β-D-呋喃呋喃糖基）咪唑5和两种或更多种复杂的磺酰胺6和7，作为嘌呤核苷酸从头生物合成的中间阶段的潜在抑制剂。5的保护形式的环化得到5-（β-D-核呋喃呋喃糖基）咪唑并[4,5 - e ] -1,2,4-噻二嗪-1,1-二氧化物8，这是腺苷和肌苷的新型类似物。
• Antitumor imidazotetrazines. 14. Synthesis and antitumor activity of 6- and 8-substituted imidazo[5,1-d]-1,2,3,5-tetrazinones and 8-substituted pyrazolo[5,1-d]-1,2,3,5-tetrazinones
  作者：Edward Lunt、Christopher G. Newton、Christopher Smith、Graham P. Stevens、Malcolm F. G. Stevens、Colin G. Straw、Roger J. A. Walsh、Peter J. Warren、Christian Fizames

  DOI：10.1021/jm00385a018

  日期：1987.2

  The systematic variation of the potent antitumor agent mitozolomide (1) is extended to cover alteration of substituents at positions 6 and 8 and to change the imidazo[5,1-d]-1,2,3,5-tetrazinone (1) skeleton to the isomeric pyrazolo-[5,1-d]-1,2,3,5-tetrazinone (17) skeleton. The series of eight 6-alkyl and 6-aralkyl derivatives of 1 showed optimal antitumor activity when the group was small or linear, but activity diminished as size and branching of this substituent increased. This may reflect altered transport characteristics, or failure of the enlarged derivatives to fit a binding site, or possibly a reduced tendency for the derivatives having bulky groups at position 6 to hydrolytically generate the putatively active triazenes (21). Testing of 14 derivatives of 1 differently substituted at position 8 revealed a complex structure-activity relationship, with good antitumor activity obtained for carbamoyl and sulfamoyl groups bearing small substituents. The 8-methylsulfonyl compound had noteworthy activity, but the 8-cyano, 8-nitro, and 8-phenyl derivatives were devoid of useful antitumor activity in these tests. From the limited number of pyrazolotetrazinones (17) reported here, it is suggested that the same conclusions as regards activity also hold true for this ring system.
• LUNT E.; NEWTON CH. G.; SMITH CH.; STEVENS G. P.; STEVENS M. F. G.; STRAW+, J. MED. CHEM., 30,(1987) N 2, 357-366
  作者：LUNT E.、 NEWTON CH. G.、 SMITH CH.、 STEVENS G. P.、 STEVENS M. F. G.、 STRAW+

  DOI：——

  日期：——