(E)-cinnamoylglycine | 16534-24-0

• 物质功能分类: 生物化工 - 氨基酸及其衍生物
• 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: (E)-cinnamoylglycine
• 英文别名: N-cinnamoylglycine；2-(cinnamamido)acetic acid；cinnamoylglycine；trans-Cinnamoyl glycine；2-[[(E)-3-phenylprop-2-enoyl]amino]acetic acid
• CAS: 16534-24-0；62430-40-4
• 化学式: C₁₁H₁₁NO₃
• mdl: MFCD00136326
• 分子量: 205.213
• InChiKey: YAADMLWHGMUGQL-VOTSOKGWSA-N

物化性质

• 熔点：
  197 °C
• 沸点：
  495.1±45.0 °C(Predicted)
• 密度：
  1.251±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2924299090
• WGK Germany：
  3
• 危险性防范说明：
  P301+P312+P330
• 危险性描述：
  H302

制备方法与用途

生物活性：Cinnamoylglycine 是人体尿液中的代谢物，一种由肉桂酸和甘氨酸结合而成的化合物。它被用作尿液标志物，在抗生素研究期后可用于标记耐药性的定殖。

靶点： | 人类内源性代谢物 |

反应信息

• 作为反应物：
  描述：

  (E)-cinnamoylglycine 在 N,N'-二异丙基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 N-cinnamoylamino glycine
  参考文献：
  名称：

  由N-酰基氨基酸通过N，N'-二异丙基碳二亚酰亚胺的环脱水和Wittig烯烃的结合一锅法合成2,4,5-三取代的恶唑。

  摘要：

  通过环化脱水的的组合ñ -酰基氨基酸与Ñ，Ñ '-diisopropylcarbodiimide（DIC）和所得到的5（4的非经典Wittig烯ħ）-oxazolones的Ph 3 P CHCN且Ph 3 P CHCOOEt，5-一锅合成恶唑乙腈和5-恶唑乙酸盐，产率分别为41-85％和57-70％。

  DOI：

  10.1016/j.tet.2011.12.004
• 作为产物：
  描述：

  肉桂酰甘氨酸甲酯 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 (E)-cinnamoylglycine
  参考文献：
  名称：

  Artificial Trinuclear Metallopeptidase Synthesized by Cross-Linkage of a Molecular Bowl with a Polystyrene Derivative

  摘要：

  A novel methodology is reported for construction of active sites of artificial multinuclear metalloenzymes: transfer of metal-chelating sites confined in a prebuilt cage to a polymeric backbone. Artificial active sites comprising two or three moieties of Cu(II) complex of tris(2-aminoethyl)amine (tren) were prepared by transfer of Cu(II)tren units confined in a molecular bowl (MB) to poly(chloromethylstyrene-co-divinylbenzene) (PCD). By treatment of unreacted chloro groups of the resulting PCD with methoxide and destruction of the MB moieties attached to PCD with acid followed by addition of Cu(II) ion to the exposed tren moieties, catalytic polymers with peptidase activity were obtained. The average number (beta) of proximal Cu(II)tren moieties in the active site of the artificial multinuclear metallopeptidase was determined by quantifying the Cu(II) content. Several species of the artificial metallopeptidases with different beta contents were prepared and examined for catalytic activity in hydrolysis of various cinnamoyl amide derivatives. The PCD-based catalytic polymers did not hydrolyze a neutral amide but effectively hydrolyzed carboxyl-containing amides (N-cinnamoyl glycine, N-cinnamoyl beta-alanine, and N-cinnamoyl gamma-amino butyrate). Analysis of the kinetic data revealed that the active sites comprising three Cu(IT)tren units were mainly responsible for the catalytic activity. When analyzed in terms of k(cat), the catalytic activity of the PCD-based artificial peptidase was comparable to or better than the catalytic antibody with the highest peptidase activity reported to date. A mechanism is suggested for the effective cooperation among the three metal centers of the active site in hydrolysis of the carboxyl-containing amides.

  DOI：

  10.1021/ja000827t

文献信息

• Molecular Mimics of Classic P-Glycoprotein Inhibitors as Multidrug Resistance Suppressors and Their Synergistic Effect on Paclitaxel
  作者：Moustafa E. El-Araby、Abdelsattar M. Omar、Maan T. Khayat、Hanan A. Assiri、Ahmed M. Al-Abd

  DOI：10.1371/journal.pone.0168938

  日期：——

  P-glycoprotein (Pgp) is a membrane bound efflux pump spread in a variety of tumor cells and considered as a main component of multidrug resistance (MDR) to chemotherapies. In this work, three groups of compounds (imidazolone, oxazolone and vinyl dipeptide derivatives) were synthesized aiming to develop a molecular framework that effectively suppresses MDR. When tested for their influence on Pgp activity, four compounds coded Cur1-01, Cur1-12V, Curox-1 and Curox-3 significantly decreased remaining ATP concentration indicating Pgp substrate site blocking. On the other hand, Cur-3 and Cur-10 significantly increased remaining ATP concentration, which is indicative of Pgp ATPase inhibition. The cytotoxicity of synthesized compounds was examined against Pgp expressing/highly resistant colorectal cancer cell lines (LS-174T). Compounds Cur-1 and Cur-3 showed considerable cytotoxicity with IC50 values of 7.6 and 8.9 μM, respectively. Equitoxic combination (at IC50 concentrations) of PTX and Cur-3 greatly diminished resistant cell clone from 45.7% to 2.5%, albeit with some drop in potency from IC50 of 7.9 nM to IC50 of 23.8 nM. On the other hand, combination of PTX and the non-cytotoxic Cur1-12V (10 μM) significantly decreased the IC50 of PTX to 3.8 nM as well as the resistant fraction to 16.2%. The combination test was confirmed using the same protocol but on another resistant CRC cell line (HCT-116) as we obtained similar results. Both Cur-3 and Cur1-12V (10 μM) significantly increased the cellular entrapment of Pgp probe (doxorubicin) elevating its intracellular concentration from 1.9 pmole/cell to 3.0 and 2.9 pmole/cell, respectively.

  P-糖蛋白（Pgp）是一种膜结合的排出泵，分布于各种肿瘤细胞中，被认为是化疗多药耐药性（MDR）的主要成分。在本研究中，合成了三组化合物（咪唑酮、噁唑酮和乙烯基二肽衍生物），旨在开发一种有效抑制MDR的分子框架。在测试它们对Pgp活性的影响时，编号为Cur1-01、Cur1-12V、Curox-1和Curox-3的四种化合物显著降低了剩余ATP浓度，表明Pgp底物结合位点被阻断。另一方面，Cur-3和Cur-10显著增加了剩余ATP浓度，这表明Pgp ATP酶受到抑制。针对表达Pgp/高度耐药的结直肠癌细胞系（LS-174T），检测了合成化合物的细胞毒性。化合物Cur-1和Cur-3显示出明显的细胞毒性，其IC50值分别为7.6和8.9 μM。等毒性组合（在IC50浓度下）的PTX和Cur-3将耐药细胞克隆从45.7%降低到2.5%，尽管其效力从IC50的7.9 nM降至23.8 nM。另一方面，PTX与非细胞毒性的Cur1-12V（10 μM）组合显著降低了PTX的IC50至3.8 nM以及耐药部分至16.2%。利用相同的协议，在另一种耐药的结直肠癌（CRC）细胞系（HCT-116）上确认了组合测试，我们获得了类似的结果。Cur-3和Cur1-12V（10 μM）显著增加了细胞内Pgp探针（多柔比星）的包裹量，使其细胞内浓度从1.9 pmole/cell分别增加到3.0和2.9 pmole/cell。
• Green Approach for the Synthesis of a New Class of Diamidomethane‐linked Benzazolyl Pyrazoles and Evaluation as Antifungals
  作者：Jyothi Sowdari、Yamini Gudi、Sowmya V. Donthamsetty、Padmavathi Venkatapuram、Padmaja Adivireddy

  DOI：10.1002/jhet.3569

  日期：2019.8

  A new class of diamidomethane‐linked benzoxazolyl pyrazoles, benzothiazolyl pyrazoles, and benzimidazolyl pyrazoles were synthesized from the synthetic intermediates N‐benzazolylcarbamoylmethylcinnamides adopting environmentally benign methods. In fact, nitrile imine was generated from araldehyde phenylhydrazone in the presence of iodosobenzene and cetyltrimethylammonium bromide followed by oxidation

  采用环境友好的方法，从合成中间体N-苯并甲唑氨甲酰甲基肉桂酰胺合成了一类新型的由二氨基甲烷连接的苯并恶唑基吡唑，苯并噻唑基吡唑和苯并咪唑基吡唑。实际上，在碘代苯和十六烷基三甲基溴化铵存在下，由芳醛苯hydr生成腈亚胺，然后在二甲基亚砜中用碘氧化。化合物的结构通过IR，1 H NMR，13 C NMR和质谱表征。还评估了标题化合物的抗真菌活性。在所有测试化合物中，苯并咪唑基吡唑基羧酰胺（13a和13b被发现是潜在的抗真菌剂。
• Cyclocondensation reactions of heterocyclic carbonyl compounds XI . Synthesis and study of cyclocondensation reactions of some 3-substituted-5-(2-aminobenzyl)-1<i>H</i>-[1,2,4]triazine-6-ones
  作者：Tomáš Guckýa、Jan Slouka、Iveta Fryšová、Michal Maloň

  DOI：10.1002/jhet.5570430314

  日期：2006.5

  (5) were also obtained by catalytic hydrogenation of corresponding nitroderivatives (4). The cyclization reaction of hydrazides (4) or (5) proceeded to 3,5-disubstituted-1,6-dihydro-[1,2,4]triazine-6-ones (6) or (7). Aminoderivatives (7) were also obtained by reduction of nitro group of compounds (6). The aminoderivatives (7) were then cyclized to 3-substituted-1,5-dihydro-[1,2,4]triazino[6,5-b]quinolines

  通过Erlenmeyer与酰基甘氨酸（1a-1i）合成2-硝基苯甲醛，制备了一系列2-取代的4-（2-硝基亚苄基）-4,5-二氢恶唑-5-酮（2a-2i），相应氨基衍生物（3B-3D和3G-3I）通过（催化加氢synthetised 2B-2D和3G-3I）。肼酮（2）和（3）的水合肼解反应得到酰肼（4）和（5）。酰肼（5）也通过相应的硝基衍生物（4）的催化氢化而获得。酰肼的环化反应（4）或（5）进行到3,5-二取代-1,6-二氢-[1,2,4]三嗪-6-一（6）或（7）。还通过还原化合物（6）的硝基获得氨基衍生物（7）。然后将氨基衍生物（7）环化为3-取代的1,5-二氢-[1,2,4]三嗪基[6,5-b]喹啉（9）。其互变异构体（10）。
• Design, Synthesis and Antiproliferative Activities of Oxidative Stress Inducers Based on 2-Styryl-3,5-dihydro-4&lt;i&gt;H&lt;/i&gt;-imidazol-4-one Scaffold
  作者：Abdelsattar M. Omar、Tamer M. Abdelghany、Mohamed S. Abdel-Bakky、Abdulrahman M. Alahdal、Mohamed F. Radwan、Moustafa E. El-Araby

  DOI：10.1248/cpb.c18-00398

  日期：2018.10.1

  kidney fibroblasts (BHK) and human lung tissue fibroblast (WI-38). Similar to trans-cinnamaldehyde, the colon cancer cell cycle analysis indicated cell cycle changes consistent with increased oxidative stress leading to apoptosis. Compound 3e caused elevation of all cell oxidative indicators of ROS such as a decrease in reduced glutathione, increased malondialdehyde and suppression of catalase and

  2-styryl-3,5-dihydro-4H-imidazol-4-one可以被认为是具有与反式肉桂醛（苯乙烯基乙醛）相似的等排特性的系统，该化合物是一种安全的天然化合物，对各种癌症均表现出令人感兴趣的活性。我们合成了一系列结构不同的化合物，它们在2-styryl-4-imidaolone药效团的N3位置具有不同的烷基，芳基和杂环取代基。测定化合物对癌症和正常细胞系的细胞毒性。另外，还研究了它们作为活性氧（ROS）诱导剂的细胞作用机理。与母体反式肉桂醛相比，许多合成的化合物在结肠癌，乳腺癌和肝癌细胞系中显示出更高的活性。化合物3a和3e在低微摩尔至亚微摩尔的IC50值下显示出对癌细胞系的选择性抗增殖活性。该化合物对正常细胞系婴儿仓鼠肾成纤维细胞（BHK）和人肺组织成纤维细胞（WI-38）的毒性极低。与反式肉桂醛相似，结肠癌细胞的细胞周期分析表明，细胞周期的变化与氧化应激的增加相一致，从而
• Pd-Oxazolone complexes conjugated to an engineered enzyme: improving fluorescence and catalytic properties
  作者：Carla Garcia-Sanz、Alicia Andreu、Blanca de las Rivas、Ana I. Jimenez、Alexandra Pop、Cristian Silvestru、Esteban P. Urriolabeitia、Jose M. Palomo

  DOI：10.1039/d1ob00305d

  日期：——

  modified enzyme variants, one containing all the natural cysteine residues changed to serine residues, and another variant including an additional Cys mutation directly in the catalytic serine (Ser114Cys). The new Pd–enzyme conjugates were fluorescent even at ppm concentrations, while under the same conditions free Pd complexes did not show fluorescence at all. The Pd conjugation with the enzyme extremely

  通过超分子Pd-氨基酸配位将不同的含正金属化推挽型恶唑酮的Pd配合物插入到两个基因工程改造的嗜热嗜热地热芽孢杆菌变体上脂肪酶（GTL）。在固相状态下，在温和条件下以固相化形式在固相上进行Pd-脂肪酶的缀合，并通过用乙腈水溶液洗涤而简单地解吸而获得可溶的缀合的Pd-GTL复合物。将三种不同的Pd复合物掺入两种不同的基因修饰的酶变体中，一种包含所有天然半胱氨酸残基变为丝氨酸残基，另一种包含直接在催化丝氨酸中的额外Cys突变（Ser114Cys）。新的Pd-酶结合物即使在ppm浓度下也能发出荧光，而在相同条件下，游离的Pd络合物根本不显示荧光。图4a的TOF值为27428min -1。还证明了在温和条件下，与原palpalpalated 4b偶联的GTL-C114在定点CH活化反应中的适用性。因此，将Pd掺入酶中产生了高度稳定的结合物，并显着提高了Pd络合物的催化活性和选择性以及荧光强度。