1-对硝基苯甲酰基-1-甲基肼 | 14908-49-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-对硝基苯甲酰基-1-甲基肼
• 英文名称: 1-p-nitrobenzoyl-1-methylhydrazine
• 英文别名: N-methyl-4-nitrobenzohydrazide；1-Methyl-1-(4-nitrobenzoyl)-hydrazin；1-Methyl-1-p-nitrobenzoylhydrazin
• CAS: 14908-49-7
• 化学式: C₈H₉N₃O₃
• mdl: MFCD18642129
• 分子量: 195.178
• InChiKey: VSGGYRBZKXGXQL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  92.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-对硝基苯甲酰基-1-甲基肼 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 4-nitrobenzoic acid 2-(1,3-dithiolan-2-ylidene)-1-methylhydrazide
  参考文献：
  名称：

  Synthesis, characterization, and tuberculostatic activity of novel 2-(4-nitrobenzoyl)hydrazinecarbodithioic acid derivatives

  摘要：

  A series of novel S-esters of 2-(4-nitrobenzoyl)hydrazinecarbodithioic acid and S,S'-diesters of (4-nitrobenzoyl)carbonohydrazonodithioic acid were synthesized by reaction of 4-nitrobenzohydrazide and N-methyl-4-nitrobenzohydrazide with carbon disulfide and alkyl halides in the presence of triethylamine. Novel 5-(4-nitrophenyl)-1,3,4-oxadiazoles were also obtained. The structures were confirmed by IR, NMR, and mass spectroscopy, and by elemental analysis. All the compounds obtained were screened in vitro for their tuberculostatic activity. Promising preliminary results were obtained for some of the compounds. The crystal structure of the most active compound was determined.

  DOI：

  10.1007/s00706-011-0708-y
• 作为产物：
  描述：

  甲基肼 、 对硝基苯甲酸 在 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 1-对硝基苯甲酰基-1-甲基肼
  参考文献：
  名称：

  Reactions of hydrazines with esters and carboxylic acids

  摘要：

  DOI：

  10.1021/jo01266a085

文献信息

• An Efficient Synthesis of Substituted Hydrazides
  作者：Alison Hulme、Hamish McNab、David Benstead、Paul Wight

  DOI：10.1055/s-2005-869858

  日期：——

  Routes for the selective synthesis of 1-, or 2-substituted hydrazides, and 1,2-disubstituted hydrazides are reported. These routes proceed via cyanoborohydride reduction of stable acyl ­hydrazone intermediates.

  报告了选择性合成一取代、二取代肼羰基化合物以及1,2-二取代肼羰基化合物的路线。这些路线通过稳定的酰基-烯酮二聚体中间体的氰基硼氢化物还原而进行。
• Synthesis of phthalazinones via palladium(ii)-catalysed intramolecular oxidative C–H/C–H cross-coupling of N′-methylenebenzohydrazides
  作者：Takanori Matsuda、Yuki Tomaru、Yoshiya Matsuda

  DOI：10.1039/c3ob40195b

  日期：——

  A palladium(II)-catalysed intramolecular oxidative C–H/C–H cross-coupling of N′-methylenebenzohydrazides to phthalazin-1(2H)-ones has been developed. This cyclization is believed to mechanistically proceed via electrophilic ortho-palladation and subsequent C-arylation of the carbon–nitrogen double bond.

  已经开发了钯（II）催化的N'-亚甲基苯甲酰肼与酞菁-1（2 H）-一的分子内氧化C-H / C-H交叉偶联。据信这种环化是通过亲电邻位钯和随后的碳-氮双键的C-芳基化而机械地进行的。
• Syntheses and antitumor activities of N′1,N′3-dialkyl-N′1,N′3-di-(alkylcarbonothioyl) malonohydrazide: The discovery of elesclomol
  作者：Shoujun Chen、Lijun Sun、Keizo Koya、Noriaki Tatsuta、Zhiqiang Xia、Timothy Korbut、Zhenjian Du、Jim Wu、Guiqing Liang、Jun Jiang、Mitsunori Ono、Dan Zhou、Andrew Sonderfan

  DOI：10.1016/j.bmcl.2013.07.032

  日期：2013.9

  A series of N'(1),N'(3)-dialkyl-N'(1),N'(3)-di(alkylcarbonothioyl) malonohydrazides have been designed and synthesized as anticancer agents by targeting oxidative stress and Hsp70 induction. Structure-activity relationship (SAR) studies lead to the discovery of STA-4783 (elesclomol), a novel small molecule that has been evaluated in a number of clinical trials as an anticancer agent in combination with Taxol. (C) 2013 Elsevier Ltd. All rights reserved.
• Synthesis and Antitumor Activity of Methyltriazene Prodrugs Simultaneously Releasing DNA-Methylating Agents and the Antiresistance Drug <i>O</i>⁶-Benzylguanine
  作者：Martin J. Wanner、Melle Koch、Gerrit-Jan Koomen

  DOI：10.1021/jm049556d

  日期：2004.12.1

  Active resistance of tumor cells against DNA alkylating agents arises by the production of high levels of the DNA repair protein O-6-alkylguanine-DNA alkyltransferase (AGT). This resistance during treatment with, for example, the anticancer agent temozolomide can be reversed by administration of O-6-benzylguanine, a purine that transfers its benzyl group to AGT and irreversibly inactivates it. Stimulated by the favorable therapeutic properties of temozolomide we designed and synthesized DNA-methylating triazenes built on the anti-resistance benzylguanine ring system. The condensation reaction between 2-nitrosopurines and acylhydrazines proved to be very suitable to prepare acylated methyltriazenes. Fine-tuning of the release rate of both the methylating agent (diazomethane) and of O-6-benzylguanine was accomplished by variation of the hydrolysis-sensitive acyl substituent in 5. Hydrolysis studies were performed with H-1 NMR and revealed that the p-nitrophenyl substituted triazene 26 showed an optimal hydrolysis rate (t(1/2) = 23 min) and almost 100% selectivity for the desired fragmentation route. In vitro antitumor studies in the 60 human tumor cell line panel of the National Cancer Institute confirmed the superior properties of p-nitrophenyl-protected methyl triazene 26, showing mean IC50 values of 10 muM compared to 100 muM for temozolomide. In analogy with temozolomide, triazene 26 showed however low preference for each of the cancer subpanels, with IC50 values between 8 and 14 muM.
• Reactions of hydrazines with esters and carboxylic acids
  作者：Richard Frederick Smith、Alvin C. Bates、Angello J. Battisti、Peter G. Byrnes、Christine T. Mroz、Thomas J. Smearing、Frederick X. Albrecht

  DOI：10.1021/jo01266a085

  日期：1968.2