N-methyl-L-4-nitrotryptophan methyl ester | 168029-90-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-methyl-L-4-nitrotryptophan methyl ester
• 英文别名: L-Tryptophan,N-methyl-4-nitro-,methyl ester；methyl (2S)-2-(methylamino)-3-(4-nitro-1H-indol-3-yl)propanoate
• CAS: 168029-90-1
• 化学式: C₁₃H₁₅N₃O₄
• 分子量: 277.28
• InChiKey: IWHMETBLPMCVNK-JTQLQIEISA-N

物化性质

• 沸点：
  482.8±45.0 °C(Predicted)
• 密度：
  1.328±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  99.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-methyl-L-4-nitrotryptophan methyl ester 在 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Synthesis and Biological Evaluations of a Series of Thaxtomin Analogues

  摘要：

  Thaxtomins are a unique family of phytotoxins with unique 4-nitroindole and diketopiperazine fragments possessing potential herbicidal activities. This work presents the total synthesis of natural product thaxtomin C and its analogues. The extensive structureactivity relationship study screens four effective compounds, including thaxtomin A and thaxtomin C. It is indicated that 4-nitro indole fragment is essential for phytotoxicity, while benzyl and m-hydroxybenzyl substituents on the diketopiperazine ring are favorable for the efficacy. The N-methylations on indole and diketopiperazine show weak influence on the herbicidal activities. The four selected compounds show effective herbicidal activities against Brassica campestris, Amaranthus retroflexus, and Abutilon theophrasti, which are comparable or better than dichlobenil, even at a dosage of 187.5 g ha(-1). Moreover, these four compounds show good crop-selective properties to different crops and exhibit moderate protoporphyrinogen oxidase (PPO) enzyme inhibition. The antifungal results indicate that thaxtomin C displays inhibition to a wide range of fungi.

  DOI：

  10.1021/jf506153t
• 作为产物：
  描述：

  methyl (2S)-2-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]-3-(4-nitro-1H-indol-3-yl)propanoate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以90%的产率得到N-methyl-L-4-nitrotryptophan methyl ester
  参考文献：
  名称：

  Synthesis and Biological Evaluations of a Series of Thaxtomin Analogues

  摘要：

  Thaxtomins are a unique family of phytotoxins with unique 4-nitroindole and diketopiperazine fragments possessing potential herbicidal activities. This work presents the total synthesis of natural product thaxtomin C and its analogues. The extensive structureactivity relationship study screens four effective compounds, including thaxtomin A and thaxtomin C. It is indicated that 4-nitro indole fragment is essential for phytotoxicity, while benzyl and m-hydroxybenzyl substituents on the diketopiperazine ring are favorable for the efficacy. The N-methylations on indole and diketopiperazine show weak influence on the herbicidal activities. The four selected compounds show effective herbicidal activities against Brassica campestris, Amaranthus retroflexus, and Abutilon theophrasti, which are comparable or better than dichlobenil, even at a dosage of 187.5 g ha(-1). Moreover, these four compounds show good crop-selective properties to different crops and exhibit moderate protoporphyrinogen oxidase (PPO) enzyme inhibition. The antifungal results indicate that thaxtomin C displays inhibition to a wide range of fungi.

  DOI：

  10.1021/jf506153t

文献信息

• Synthesis of thaxtomin C
  作者：Russell R. King

  DOI：10.1139/v97-140

  日期：1997.9.1

  N-Methyl-L-4-nitrotryptophan methyl ester (2) and t-Boc- L-phenylalanine (3) were condensed to form the dipeptide 4, which was then cyclized to give 12-N-methylcyclo-(L-4-nitrotryptophyl-L-phenylalanyl) (1), a.k.a. thaxtomin C, the principle phytotoxin associated with Streptomycesipomoeae. Keywords: Streptomycesipomoeae, phytotoxin, thaxtomin C.

  N-甲基-L-4-硝基色氨酸甲酯（2）和t-Boc-L-苯丙氨酸（3）缩合形成二肽4，然后环化形成12-N-甲基环-（L-4-硝基色氨酸基-L-苯丙氨酰基）（1），也称为thaxtomin C，是与Streptomycesipomoeae相关的主要植物毒素。关键词：Streptomycesipomoeae，植物毒素，thaxtomin C。
• 4-Nitrotrypophans associated with the in vitro production of thaxtomin A by Streptomyces scabies
  作者：Russell R. King、C. Harold Lawrence

  DOI：10.1016/0031-9422(95)00256-7

  日期：1995.9

  Non-phytotoxic exudates associated with the in vitro production of thaxtomin A by Streptomyces scabies yielded two 4-nitrotryptophan derivatives, N-acetyl-4-nitrotryptophan and N-methyl-4-nitrotryptophan.

  与 Streptomyces scabies 体外产生 thaxtomin A 相关的非植物毒性渗出物产生两种 4-硝基色氨酸衍生物，N-乙酰-4-硝基色氨酸和 N-甲基-4-硝基色氨酸。
• US20140275541A1
  申请人：——

  公开号：US20140275541A1

  公开（公告）日：2014-09-18
• US8993762B2
  申请人：——

  公开号：US8993762B2

  公开（公告）日：2015-03-31
• Synthesis and Biological Evaluations of a Series of Thaxtomin Analogues
  作者：Hongbo Zhang、Qingpeng Wang、Xin Ning、Hang Hang、Jing Ma、Xiande Yang、Xiaolin Lu、Jiabao Zhang、Yonghong Li、Congwei Niu、Haoran Song、Xin Wang、Peng George Wang

  DOI：10.1021/jf506153t

  日期：2015.4.15

  Thaxtomins are a unique family of phytotoxins with unique 4-nitroindole and diketopiperazine fragments possessing potential herbicidal activities. This work presents the total synthesis of natural product thaxtomin C and its analogues. The extensive structureactivity relationship study screens four effective compounds, including thaxtomin A and thaxtomin C. It is indicated that 4-nitro indole fragment is essential for phytotoxicity, while benzyl and m-hydroxybenzyl substituents on the diketopiperazine ring are favorable for the efficacy. The N-methylations on indole and diketopiperazine show weak influence on the herbicidal activities. The four selected compounds show effective herbicidal activities against Brassica campestris, Amaranthus retroflexus, and Abutilon theophrasti, which are comparable or better than dichlobenil, even at a dosage of 187.5 g ha(-1). Moreover, these four compounds show good crop-selective properties to different crops and exhibit moderate protoporphyrinogen oxidase (PPO) enzyme inhibition. The antifungal results indicate that thaxtomin C displays inhibition to a wide range of fungi.