N-carbamoylputrescine hydrochloride | 92334-58-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机碳酸及其衍生物
• 英文名称: N-carbamoylputrescine hydrochloride
• 英文别名: 4-aminobutylurea hydrochloride；(4-amino-butyl)-urea; hydrochloride；(4-Amino-butyl)-harnstoff; Hydrochlorid；(4-Aminobutyl)urea hydrochloride；4-aminobutylurea;hydrochloride
• CAS: 92334-58-2
• 化学式: C₅H₁₃N₃O*ClH
• mdl: MFCD19382029
• 分子量: 167.639
• InChiKey: LRLBYNXGTCDIHF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.36
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  81.1
• 氢给体数：
  4
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N2-[芴甲氧羰基]-L-赖氨酸烯丙酯单盐酸盐 、 (S)-2-乙酰胺基-6-((叔丁氧羰基)氨基)己酸 、 N-carbamoylputrescine hydrochloride 在 2-chlorotrityl chloride polystyrene resin 、 N,N-二异丙基乙胺 、 哌啶 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.67h， 生成 (2S)-2-acetamido-6-amino-N-[(2S)-6-amino-1-[4-(carbamoylamino)butylamino]-1-oxohexan-2-yl]hexanamide
  参考文献：
  名称：

  Substrate-based peptidomimetic inhibitors of the Murray Valley encephalitis virus NS2B/NS3 serine protease: A P1–P4 SAR study

  摘要：

  Murray Valley encephalitis is an infectious disease spread by a mosquito-borne virus endemic in Papua New Guinea and northern Australia. In the past decade, it has spread to various regions of Australia and there is currently no therapeutic treatment against this disease. An attractive drug target is the viral serine protease NS2B/NS3, a critical enzyme involved in viral replication. Herein, we report the inhibitory activities of 37 C-terminal agmatine peptidomimetic inhibitors which led to the design of a novel structurally-constrained competitive inhibitor 38 possessing a K-i of 2.5 +/- 0.5 mu M. We believe our data provides crucial insights into the viral protease active site specificity which could be used to facilitate drug design against Murray Valley encephalitis viral infections. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.07.028
• 作为产物：
  描述：

  potassium cyanate 、 四亚甲基二胺 在 三氟乙酸 、 盐酸 作用下， 以 乙醇 、 甲醇 为溶剂， 反应 2.0h， 以0.74 g的产率得到N-carbamoylputrescine hydrochloride
  参考文献：
  名称：

  N-Carbamoylputrescine, a citrulline-derived polyamine, is not a significant citrulline metabolite in rats

  摘要：

  Citrulline, a key amino acid of the urea cycle, has been shown to play a regulatory role in protein and energy metabolism in mammals. We questioned whether N-carbamoyl-putrescine (NCP), the decarboxylated derivative of citrulline, could play a role in the biological properties of this amino acid. To evidence the presence of NCP in mammalian tissues, we developed a sensitive reverse-phase high-performance liquid chromatography (HPLC) with fluorimetric detection method with precolumn dansyl derivatization and solid-phase extraction for the determination of NCP together with polyamines in biological samples. Dansyl NCP was identified with a 5.85-min retention time. Linearity was obtained in a concentration range of 0.125 to 12.5 mu M. Intraday and day-to-day relative coefficients of variation ranged from 8.9% to 12.3% and from 14% to 14.3%, respectively. Recovery rates in serum ranged from 75% to 83%. Thereafter, we used this method to search for the presence of NCP in serum, muscle, liver, jejunum, and ileum in rats after both short-term intraperitoneal injection and long-term oral citrulline supplementation. We failed to detect NCP in these animals. These data suggest that NCP is not a significant citrulline metabolite in rats. (C) 2012 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.ab.2011.12.040

文献信息

• Substrate-based peptidomimetic inhibitors of the Murray Valley encephalitis virus NS2B/NS3 serine protease: A P1–P4 SAR study
  作者：Melgious Jin Yan Ang、Gerald Han Jie Yong、Anders Poulsen、Siew Wen Then、Zhitao Li、Joma Joy、Jeffrey Hill、Cheng San Brian Chia

  DOI：10.1016/j.ejmech.2013.07.028

  日期：2013.10

  Murray Valley encephalitis is an infectious disease spread by a mosquito-borne virus endemic in Papua New Guinea and northern Australia. In the past decade, it has spread to various regions of Australia and there is currently no therapeutic treatment against this disease. An attractive drug target is the viral serine protease NS2B/NS3, a critical enzyme involved in viral replication. Herein, we report the inhibitory activities of 37 C-terminal agmatine peptidomimetic inhibitors which led to the design of a novel structurally-constrained competitive inhibitor 38 possessing a K-i of 2.5 +/- 0.5 mu M. We believe our data provides crucial insights into the viral protease active site specificity which could be used to facilitate drug design against Murray Valley encephalitis viral infections. (C) 2013 Elsevier Masson SAS. All rights reserved.
• N-Carbamoylputrescine, a citrulline-derived polyamine, is not a significant citrulline metabolite in rats
  作者：D. Ramani、S. Nakib、H. Chen、C. Garbay、A. Loukaci、L. Cynober、J.P. De Bandt

  DOI：10.1016/j.ab.2011.12.040

  日期：2012.4

  Citrulline, a key amino acid of the urea cycle, has been shown to play a regulatory role in protein and energy metabolism in mammals. We questioned whether N-carbamoyl-putrescine (NCP), the decarboxylated derivative of citrulline, could play a role in the biological properties of this amino acid. To evidence the presence of NCP in mammalian tissues, we developed a sensitive reverse-phase high-performance liquid chromatography (HPLC) with fluorimetric detection method with precolumn dansyl derivatization and solid-phase extraction for the determination of NCP together with polyamines in biological samples. Dansyl NCP was identified with a 5.85-min retention time. Linearity was obtained in a concentration range of 0.125 to 12.5 mu M. Intraday and day-to-day relative coefficients of variation ranged from 8.9% to 12.3% and from 14% to 14.3%, respectively. Recovery rates in serum ranged from 75% to 83%. Thereafter, we used this method to search for the presence of NCP in serum, muscle, liver, jejunum, and ileum in rats after both short-term intraperitoneal injection and long-term oral citrulline supplementation. We failed to detect NCP in these animals. These data suggest that NCP is not a significant citrulline metabolite in rats. (C) 2012 Elsevier Inc. All rights reserved.