2-methoxyimino-3-phenylpropionic acid | 35031-41-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: 2-methoxyimino-3-phenylpropionic acid
• 英文别名: 3-Phenyl-2-methoximino-propansaeure；2-Methoxyimino-3-phenylpropionsaeure；2-Methoxyimino-3-phenylpropanoic acid；2-methoxyimino-3-phenylpropanoic acid
• CAS: 35031-41-5
• 化学式: C₁₀H₁₁NO₃
• 分子量: 193.202
• InChiKey: WXBHHXLWEQRNKX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  58.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-methoxyimino-3-phenylpropionic acid 在 氯化亚砜 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 三乙胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 40.0h， 生成 rac-(E)-cyclo[N-methyloxy-2-(phenylmethylene)glycylprolyl]
  参考文献：
  名称：

  环状二肽亚芳基N-烷氧基二酮哌嗪的合成及活性评价

  摘要：

  设计了一系列芳基N-烷氧基二酮哌嗪并通过肟醚形成和分子内酰化立体合成。讨论了可能的环化和酸催化的重排-断裂机理。新型二酮哌嗪的晶体结构进一步证实了重排机理。大多数化合物表现出抗肿瘤活性。几种化合物对caspase-3更有效。具体而言，化合物6e，6g和6f在IC 50上抑制caspase-3值在低微摩尔范围内，并显示出良好的选择性。基于分子对接的结果，还讨论了烷氧基二酮哌嗪在caspase-3活性中心的结合方式。

  DOI：

  10.1016/j.bmc.2016.08.038
• 作为产物：
  描述：

  2-苄基乙酰乙酸乙酯 在 sodium hydroxide 、 亚硝酸乙酯 、 sodium ethanolate 、 potassium carbonate 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 7.0h， 生成 2-methoxyimino-3-phenylpropionic acid
  参考文献：
  名称：

  Design, synthesis, and anti-tumor activity of (2-O-alkyloxime-3-phenyl)-propionyl-1-O-acetylbritannilactone esters

  摘要：

  The extracts of Inula britannica have anti-inflammatory, anti-bacterial, anti-hepatitic, and anti-tumor activities. Various sesquiterpene lactones with cytotoxic properties including 1-O-acetylbritannilactone (1) have been isolated from this Chinese medicinal plant. Eight derivatives of 1-O-acetylbritannilactone, (2-O-alkyloxime-3-phenyl)-propionyt-1-O-acetylbritannilactone esters were designed and synthesized. Four of these compounds were tested to show inhibitory activity on the growth of human leukemia HL-60 and cancer Bel-7402 cell lines. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.02.024

文献信息

• Synthesis and structure-activity study of protease inhibitors. IV. Amidinonaphthols and related acyl derivatives.
  作者：TAKUO AOYAMA、TOSHIYUKI OKUTOME、TOYOO NAKAYAMA、TAKASHI YAEGASHI、RYOJI MATSUI、SHIGEKI NUNOMURA、MASATERU KURUMI、YOJIRO SAKURAI、SETSURO FUJII

  DOI：10.1248/cpb.33.1458

  日期：——

  Various amidinonaphthols and their acyl derivatives were synthesized and evaluated for inhibitory activities against trypsin, plasmin, kallikrein, thrombin, Clr and Cls, as well as against in vitro complement-mediated hemolysis. 6-Amidino-2-naphthyl 4-guanidinobenzoate (74, FUT-175) was found to have potent inhibitory activities, particularly against trypsin (IC50 : 0.02 μM), Clr (IC50 : 0.1 μM) and Cls (IC50 : 0.02 μM), and to be highly effective in inhibiting the complement-mediated hemolysis (IC50 : 0.03μM). FUT-175, furthermore, showed considerable effectiveness in the systemic Forssman shock reaction, in which involvement of the complement system as the pathogenetic factor is well established.

  合成了多种 amidinonaphthol 及其酰基衍生物，并评估了它们对胰蛋白酶、纤溶酶、激肽释放酶、凝血酶、Clr 和 Cls 以及体外补体介导溶血的抑制活性。发现 6-Amidino-2-萘基 4-胍基苯甲酸酯（74，FUT-175）具有强大的抑制活性，尤其对胰蛋白酶（IC50：0.02 μM）、Clr（IC50：0.1 μM）和 Cls（IC50：0.02 μM），并且在抑制补体介导溶血方面非常有效（IC50：0.03 μM）。此外，FUT-175 在全身性福斯曼休克反应中显示出显著的疗效，该反应中补体系统作为致病因素的作用已被充分证实。
• Aerothionin and homoaerothionin: two tetrabromo spirocyclohexadienylisoxazoles from Verongia sponges
  作者：K. Moody、R. H. Thomson、E. Fattorusso、L. Minale、G. Sodano

  DOI：10.1039/p19720000018

  日期：——

  Aerothionin and homoaerothionin, tetrabromo-compounds from the sponges V. thiona and V. aerophoba are shown to be the homologous spirocyclohexadienylisoxazoles (XIII) and (XIV), respectively.

  来自海绵V. thiona和V. aerophoba的四溴代化合物Aerothionin和homaerothionin分别是同源的螺环己二烯基异恶唑（XIII）和（XIV）。
• Stereoselective synthesis and rearrangement-fragmentation of arylidene N-alkoxydiketopiperazines
  作者：Shouxin Liu、Yun Mu、Jianrong Han、Xiaoli Zhen、Yihua Yang、Xia Tian、Andrew Whiting

  DOI：10.1039/c1ob05722g

  日期：——

  A stereoselective synthesis of arylidene N-alkoxydiketopiperazines viaoxime-ether formation and intramolecular acylation is described, followed by an acid-catalysed rearrangement-fragmentation to give novel diketopiperazine hemiaminal derivatives with useful bioactivity against certain tumour cell lines.

  描述了通过肟-醚形成和分子内酰化立体选择性合成芳基N-烷氧基二酮哌嗪类化合物，然后进行酸催化的重排-片段化反应，从而得到新颖的二酮哌嗪类半胱氨酸衍生物，其对某些肿瘤细胞系具有有用的生物活性。
• Design, Synthesis, and Antitumor Activity of Novel Acylate of 6-OH at 1- O-acetylbritannilactone
  作者：Shouxin Liu、Jun Feng、He Liu、Junzhang Li、Xia Tian

  DOI：10.2174/1573406410666140815123216

  日期：2015.1.30

  N-(α-Alkyloxime-3-phenylpropionyl) proline was designed and synthesized as an acylating agent to modify the 6-OH of 1-O-acetylbritannilactone. Eight intermediates and eight target compounds were obtained. The structures of sixteen novel compounds were characterized by 1HNMR, IR and HRMS. The activities against HL-60 and Bel-7402 cell lines were tested, the IC50 values of compound IVg were 2.7 μM and 4.3 μM, respectively.

  设计并合成了 N-(α-烷氧基肟-3-苯基丙酰基)脯氨酸作为酰化剂，用于修饰 1-O-acetylbritannilactone 的 6-OH。共得到 8 个中间体和 8 个目标化合物。通过 1HNMR、IR 和 HRMS 对 16 种新型化合物的结构进行了表征。测试了化合物 IVg 对 HL-60 和 Bel-7402 细胞株的活性，其 IC50 值分别为 2.7 μM 和 4.3 μM。
• Assembly of Indoline-2-carboxylate-Embodied Dipeptides via Pd-Catalyzed C(sp²)–H Bond Direct Functionalization
  作者：Yu-Peng He、Chao Zhang、Mengyang Fan、Zhijie Wu、Dawei Ma

  DOI：10.1021/ol503514t

  日期：2015.2.6

  Intramolecular dehydrogenative cyclization of 2-methoxyiminoacyl-protected phenylalanine derivatives proceeded at 110 °C under catalysis of Pd(OAc)2 in the presence of 1-fluoro-2,4,6-trimethylpyridinium tetrafluoroborate to afford substituted indoline-2-carboxylates that were converted into indoline-2-carboxylate-embodied dipeptides via Raney Ni-catalyzed hydrogenation.