4-(N,N-dimethylamino)-N'-(6-hydroxyhexyl)benzamide | 792936-62-0

• 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-(N,N-dimethylamino)-N'-(6-hydroxyhexyl)benzamide
• 英文别名: Benzamide, 4-(dimethylamino)-N-(6-hydroxyhexyl)-；4-(dimethylamino)-N-(6-hydroxyhexyl)benzamide
• CAS: 792936-62-0
• 化学式: C₁₅H₂₄N₂O₂
• 分子量: 264.368
• InChiKey: CZPAIZPJGAENSL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  52.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(N,N-dimethylamino)-N'-(6-hydroxyhexyl)benzamide 在 四溴化碳 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 生成 N-(6-Bromo-hexyl)-4-dimethylamino-benzamide
  参考文献：
  名称：

  人组蛋白脱乙酰基酶的新型抑制剂：基于SAHA的非异羟肟酸酯的设计，合成，酶抑制和癌细胞生长抑制。

  摘要：

  为了找到新型的非异羟肟酸酯组蛋白脱乙酰基酶（HDAC）抑制剂，设计并合成了以亚磺酰苯胺异羟肟酸（SAHA）为模型的一系列化合物。在该系列中，发现化合物7（其中SAHA的异羟肟酸被硫醇替代）与SAHA一样有效，该系列的优化导致鉴定出比SAHA更有效的HDAC抑制剂。在癌细胞生长抑制测定中，S-异丁酰基衍生物51显示出强活性，并且其效力与SAHA相当。通过Western印迹分析证实癌细胞生长抑制活性是组蛋白过度乙酰化和随后诱导p21（WAF1 / CIP1）的结果。

  DOI：

  10.1021/jm049207j
• 作为产物：
  描述：

  4-二甲氨基苯甲酸 在 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 3.0h， 生成 4-(N,N-dimethylamino)-N'-(6-hydroxyhexyl)benzamide
  参考文献：
  名称：

  Development and characterization of improved β-lactone-based anti-virulence drugs targeting ClpP

  摘要：

  Here, we report the synthesis and in depth characterization of a second generation B-lactone derived virulence inhibitors. Based on initial results that emphasized the intriguing possibility to disarm bacteria in their virulence the present study develops this concept further and analyses the potential of this strategy for drug development. We were able to expand the collection of bioactive compounds via an efficient synthetic route. Testing of all compounds revealed several hits with anti-virulence activity. Moreover, we demonstrated that these molecules act solely by reducing virulence but not killing bacteria which is an important prerequisite for preserving the useful microbiome. Finally, incubation of lactones with eukaryotic cell lines indicated a tolerable cytotoxicity which is essential for entering animal studies. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.07.047

文献信息

• An Antibacterial β-Lactone Kills Mycobacterium tuberculosis by Disrupting Mycolic Acid Biosynthesis
  作者：Johannes Lehmann、Tan-Yun Cheng、Anup Aggarwal、Annie S. Park、Evelyn Zeiler、Ravikiran M. Raju、Tatos Akopian、Olga Kandror、James C. Sacchettini、D. Branch Moody、Eric J. Rubin、Stephan A. Sieber

  DOI：10.1002/anie.201709365

  日期：2018.1.2

  potent anti‐mycobacterial and bactericidal activity. Chemical proteomics using an alkynylated probe identified Pks13 and Ag85 serine hydrolases as major targets. Validation through enzyme assays and customized 13C metabolite profiling showed that both targets are functionally impaired by the β‐lactone. Co‐administration with front‐line antibiotics enhanced the potency against M. tuberculosis by more than

  抗生素抗性的传播是治疗结核分枝杆菌感染的主要挑战。另外，药物的功效常常受到肌膜通透性的限制。一线抗生素抑制肌膜生物合成，导致细胞快速死亡。受此机制的启发，我们将β-内酯用作推定的霉菌酸模拟物，以阻断参与其生物合成的丝氨酸水解酶。在一系列β-内酯中，我们发现一种具有强大的抗分枝杆菌和杀菌活性的产品。使用烷基化探针的蛋白质组学将Pks13和Ag85丝氨酸水解酶鉴定为主要靶标。通过酶分析验证和定制13C代谢产物谱分析表明，两个目标均受到β-内酯的功能损害。与一线抗生素共同给药可将抗结核分枝杆菌的效力提高100倍以上，从而证明了靶向肌膜生物合成丝氨酸水解酶的治疗潜力。
• UV-ABSORBING COMPOUNDS WITH AT LEAST ONE REACTIVE HYDROGEN
  申请人：ISP INVESTMENTS INC.

  公开号：US20160002154A1

  公开（公告）日：2016-01-07

  UV-absorbing compounds are provided that have at least one reactive hydrogen. These compounds have structures: wherein the generic notations have meanings as described herein. Also provided are formulations comprising a UV-absorbing compounds.

  提供具有至少一个反应性氢的UV吸收化合物。这些化合物具有以下结构：其中通用符号的含义如本文所述。还提供了包含UV吸收化合物的配方。
• UV-absorbing compounds with at least one reactive hydrogen
  申请人：ISP INVESTMENTS LLC

  公开号：US10351523B2

  公开（公告）日：2019-07-16

  UV-absorbing compounds are provided that have at least one reactive hydrogen. These compounds have structures: wherein the generic notations have meanings as described herein. Also provided are formulations comprising a UV-absorbing compounds.

  所提供的紫外线吸收化合物至少含有一个活性氢。这些化合物的结构如下 其中通用符号的含义如本文所述。此外，还提供了包含紫外线吸收化合物的配方。
• Thiol-based SAHA analogues as potent histone deacetylase inhibitors
  作者：Takayoshi Suzuki、Akiyasu Kouketsu、Azusa Matsuura、Arihiro Kohara、Shin-ichi Ninomiya、Kohfuku Kohda、Naoki Miyata

  DOI：10.1016/j.bmcl.2004.03.063

  日期：2004.6

  In order to find novel nonhydroxamate histone deacetylase (HDAC) inhibitors, a series of thiol-based compounds modeled after suberoylanilide hydroxamic acid (SAHA) was synthesized, and their inhibitory effect on HDACs was evaluated. Compound 6, in which the hydroxamic acid of SAHA was replaced by a thiol, was found to be as potent as SAHA, and optimization of this series led to the identification of HDAC inhibitors more potent than SAHA. (C) 2004 Elsevier Ltd. All rights reserved.
• [EN] UV-ABSORBING COMPOUNDS WITH AT LEAST ONE REACTIVE HYDROGEN<br/>[FR] COMPOSÉS ABSORBANT L'ULTRAVIOLET COMPRENANT AU MOINS UN HYDROGÈNE RÉACTIF
  申请人：ISP INVESTMENTS INC

  公开号：WO2014149363A1

  公开（公告）日：2014-09-25

  UV-absorbing compounds are provided that have at least one reactive hydrogen. These compounds have structures: wherein the generic notations have meanings as described herein. Also provided are formulations comprising a UV-absorbing compounds.