N-丁基-2-氯-5-硝基苯甲酰胺 | 68505-92-0

• 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: N-丁基-2-氯-5-硝基苯甲酰胺
• 英文名称: 2-chloro-5-nitro-N-butylbenzamide
• 英文别名: N-Butyl-2-chloro-5-nitrobenzamide；<2-Chlor-5-nitro-benzoesaeure>-butylamid
• CAS: 68505-92-0
• 化学式: C₁₁H₁₃ClN₂O₃
• mdl: MFCD01215255
• 分子量: 256.689
• InChiKey: YDKDPVDEANOMEE-UHFFFAOYSA-N

物化性质

• 熔点：
  136 °C
• 沸点：
  377.6±32.0 °C(Predicted)
• 密度：
  1.263±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  74.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-丁基-2-氯-5-硝基苯甲酰胺 在 sodium tetrahydroborate 、 palladium 10% on activated carbon 、 sodium hydride 、 三乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 水 、 mineral oil 为溶剂， 反应 9.0h， 生成 5-(2-bromoacetamido)-N-butyl-2-(p-chlorophenoxy)benzamide
  参考文献：
  名称：

  Synthesis of benzamide derivatives and their evaluation as antiprion agents

  摘要：

  A new set of 5-(2-(pyrrolidin-1-yl)acetamido)-N-butyl-2-(substituted) benzamide and 5-(2-(piperidin-1-yl)acetamido)-N-butyl-2-(substituted) benzamide derivatives were synthesized in which as structural features the 2-(1-pyrrolidinyl)- or 2-(1-piperidyl) acetylamino group or a diphenylether moiety are associated to a benzamide scaffold. Their binding affinity for human PrPC and inhibition of its conversion into PrPSc were determined in vitro; moreover, the antiprion activity was assayed by inhibition of PrPSc accumulation in scrapie-infected mouse neuroblastoma cells (ScN2a) and scrapie mouse brain (SMB) cells. The results clearly indicate the benzamide derivatives as attractive lead compounds for the development of potential therapeutic agents against prion disease. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.06.026
• 作为产物：
  描述：

  2-氯-5-硝基苯甲酸 在 氯化亚砜 、 碳酸氢钠 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 3.0h， 生成 N-丁基-2-氯-5-硝基苯甲酰胺
  参考文献：
  名称：

  Shinde; Shenoy; Pai, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1990, vol. 29, # 8, p. 711 - 720

  摘要：

  DOI：

文献信息

• One Pot Regioselective Synthesis of a Small Library of Dibenzo[<i>b</i>,<i>f</i>][1,4]thiazepin-11(10<i>H</i>)-ones via Smiles Rearrangement
  作者：Yongmei Zhao、Qiaoling Dai、Zhi Chen、Qihui Zhang、Yongcheng Bai、Chen Ma

  DOI：10.1021/co300139s

  日期：2013.2.11

  A facile and efficient method has been developed for the synthesis of a small library of dibenzo[b,f][1,4]thiazepin-11(10H)-ones via Smiles rearrangement. Compounds were obtained in excellent isolated yields (70%–92%) under metal-free conditions. More specifically, this transition metal-free process relates to an environmentally friendly, economical, and efficient method for preparing benzoic-fused

  已经开发了一种通过Smiles重排合成小的二苯并[ b，f ] [1,4] thiazepin-11（10 H）-ones小型文库的简便有效方法。在无金属条件下，化合物的分离产率极高（70％–92％）。更具体地说，这种无过渡金属的方法涉及制备苯并稠合的七元内酰胺的环保，经济和有效的方法。
• Synthesis of substituted benzamides as anti-inflammatory agents that inhibit preferentially cyclooxygenase 1 but do not cause gastric damage
  作者：G Caliendo

  DOI：10.1016/s0223-5234(01)01251-x

  日期：2001.6

  Parsalmide (5-amino-N-butyl-2-(2-propynyloxy) benzamide) (5a), is a non-steroidal anti-inflammatory drug (NSAID), commercialised in Italy until 1985 with the brand name of Synovial(R), that has been widely used to treat arthritic patient. In addition, it was shown to spare gastric mucosa. Here we have synthesised a series of novel substituted benzamides, related to Parsalmide, and have evaluated their activity in vitro on COX-1 and COX-2 as well as in vivo in the carrageenin-induced rat paw edema, a classical in vivo anti-inflammatory assay. Compounds 5b, 11a and 11b, which showed a favourable profile in vitro and in vivo, were screened in comparison with Parsalmide for gastrointestinal (GI) tolerability in vivo in the rat. Results obtained showed that Parsalmide and compound 11b inhibited both COX-1 and COX-2 in vitro as well as they were active in vivo. Both compounds were devoid of gastric effect at the efficacious dose. In addition, both prevented indomethacin-induced gastric damage. Thus, these compounds may guide the definition of a new leading structure with anti-inflammatory activity that may allow designing new safer NSAIDs. (C) 2001 Editions scientifiques et medicales Elsevier SAS.
• In vitro mutagenicity of anti-inflammatory parsalmide analogues PA7, PA10, and PA31 triggered by biotransformation into hydroxy derivatives
  作者：H.S. Cardoso、B. Bicalho、P. Genari、V. Santagada、G. Caliendo、E. Perissutti、J.L. Donato、G. De Nucci

  DOI：10.1016/j.ejmech.2005.10.019

  日期：2006.3

  In this study, the mutagenicity of the anti-inflammatory parsalmide [5-amino-N-butyl-2-(2-propynyloxy)-benzamide] analogues PA7 [5-amino-N-butyl-2-cyclohexyloxy-benzamide], PA10 [5-amino-N-butyl-2-phenoxy-benzamide] and PA31 [5-amino-N-butyl-2-(p-tolyloxy)-benzamide] was determined by an Ames Salmonella assay. The experiments were performed by preincubating the compounds in the absence and presence of a post-mitochondrial fraction (S9) of rat liver homogenate from phenobarbital/beta-naphtoflavone treated rats. No mutagenic effect was observed after direct testing (no S9 added) in Salmonella typhymurium strains TA98, TA100, TA102, TA1535 and TA1537. However, in the presence of S9, the test substances triggered mutagenic responses in strains TA100 and TA98. PA31 presented the strongest mutagenic potential. The reversion rates in the presence of PA31 were about 2-19 fold higher than spontaneous mutation rates. In the presence of PA7, the reversion increased 2-14-fold over spontaneous rates. While PA10 showed a relatively mild mutagenic potential, as the number of revertants did not exceed 2.5 times the number of spontaneous mutations. Mass spectrometric analysis of the in vitro biotransformation showed that S9 converted (%), regioselectively, PA7 (19%), PAIO (7%) and PA31 (12%) into hydroxy-derivatives. (c) 2006 Elsevier SAS. All rights reserved.
• Synthesis of 2-Alkoxy-5-nitrobenzamides by Phase-Transfer Catalyzed Nucleophilic Substitution of 2-Chloro-5-nitrobenzamides
  作者：Dino Nisato、Marco Frigerio、Giovanni Boccardi、Giovanni Palmisano

  DOI：10.1055/s-1982-30077

  日期：——
• DE654467
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