(E)-Cinnamamide
(Synonyms: 肉桂酰胺) 目录号 : GC60401
(E)-Cinnamamide是Cinnamamide的低活性异构体。Cinnamamide是Cinnamicacid的衍生物。Cinnamamide作为一种非致命的化学驱虫剂，可有效降低禽害虫的危害。
Cas No.:22031-64-7
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
(E)-Cinnamamide, the less active isomer of Cinnamamide. Cinnamamide, a derivative of the plant secondary compound Cinnamic acid. Cinnamamide is effectiveness as a non-lethal chemical repellent suitable for reducing avian pest damage[1].
[1]. Richard W. Watkins, et al. Evaluation of cinnamamide as an avian repellent: Determination of a dose—response curve.
| Cas No. | 22031-64-7 | SDF | |
| 别名 | 肉桂酰胺 | ||
| Canonical SMILES | O=C(N)/C=C/C1=CC=CC=C1 | ||
| 分子式 | C9H9NO | 分子量 | 147.17 |
| 溶解度 | 储存条件 | Store at -20°C | |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 6.7949 mL | 33.9743 mL | 67.9486 mL |
| 5 mM | 1.359 mL | 6.7949 mL | 13.5897 mL |
| 10 mM | 0.6795 mL | 3.3974 mL | 6.7949 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
N-(4-Nitro-phen-yl)cinnamamide
Acta Crystallogr Sect E Struct Rep Online 2009 Aug 8;65(Pt 9):o2068.PMID:21577491DOI:10.1107/S1600536809030049.
In the mol-ecule of the title compound, C(15)H(12)N(2)O(3), the dihedral angle between the rings is 3.04 (8)°. The central NOC(3) fragment is planar [maximum deviation = 0.005 (3) Å] and is oriented at dihedral angles of 8.23 (8) and 7.29 (9)° with respect to the phenyl and nitro-phenyl rings, respectively. In the crystal structure, inter-molecular N-H⋯O and C-H⋯O inter-actions link the mol-ecules into a two-dimensional network. π-π contacts between rings [centroid-centroid distance = 3.719 (1) Å] may further stabilize the structure.
Four N-(E)-cinnamoyl (cinnamamide) derivatives of aminoalkanols with promising anticonvulsant and analgesic activity
Bioorg Med Chem Lett 2019 Jun 1;29(11):1298-1303.PMID:30975624DOI:10.1016/j.bmcl.2019.04.006.
Epilepsy and neuropathic pain are frequent neurological disorders with pathomechanism based on abnormal neuronal discharges. Secondary tissue impairment observed after traumatic brain injury is also connected with neuronal dysfunction. Those three neurological disorders are ineffectively treated with currently available pharmacotherapy options so great effort is made in searching for new effective drugs. Four N-(E)-cinnamoyl (cinnamamide) derivatives of aminoalkanols: S-(2E)-N-(1-hydroxypropan-2-yl)-3-(2-methylphenyl)prop-2-enamide (1), R,S-(2E)-3-(4-chlorophenyl)-N-(1-hydroxybutan-2-yl)prop-2-enamide (2), R,S-(2E)-3-(4-chlorophenyl)-N-(2-hydroxypropyl)prop-2-enamide (3), (2E)-3-(4-chlorophenyl)-N-(4-hydroxycyclohexyl)prop-2-enamide (4) were evaluated in vivo and in vitro for anticonvulsant, neuroprotective and/or analgesic activity. In intravenous metrazol seizure threshold test compounds 1-3 did not show pro-convulsive effect but proved anticonvulsant potential. In corneal kindled mice model the tested compounds showed beneficial anticonvulsant properties with ED50 of 36.8 mg/kg for 1, 25.7 mg/kg for 2, and 51.1 mg/kg for 3. Compound 2 tested in vitro in spontaneously bursting rat hippocampal slice model significantly reduced burst rate. Compounds 1 and 2 did not decrease lesion volume in acute model of traumatic brain injury. In formalin test of hyperalgesia in mice, compound 1 was active in the acute phase of the test, while compound 4 caused reduction of the time of licking of the affected paw by approx. 88% during the acute phase and 100% during the inflammatory phase. In rat sciatic ligation model of neuropathic pain, compound 1 significantly increased the paw withdrawal threshold starting from one hour after oral administration and the activity continued up to six hours. Reported here four N-(E)-cinnamoyl derivatives of aminoalkanols possess promising activity as anticonvulsant and/or analgesic agents.
Mechanistic Unveiling of C═C Double-Bond Rotation and Origins of Regioselectivity and Product E/Z Selectivity of Pd-Catalyzed Olefinic C-H Functionalization of (E)-N-Methoxy Cinnamamide
J Org Chem 2018 Feb 16;83(4):2067-2076.PMID:29376365DOI:10.1021/acs.joc.7b03007.
Density functional theory (DFT) calculations have been performed to study the Pd-catalyzed C-H functionalization of (E)-N-methoxy cinnamamide (E1), which selectively provides the α-C-H activation products (EP as minor product and its C═C rotation isomer ZP' as major product). Three crucial issues are solved: (i) The detailed mechanism leading to ZP' is one issue. The computational analyses of the mechanisms proposed in previously experimental and theoretical literature do not seem to be consistent with the experimental findings due to the high barriers involved. Alternatively, we present a novel oxidation/reduction-promoted mechanism featuring the Pd(0) → Pd(II) → Pd(0) transformation. The newly proposed mechanism involves the initial coordination of the active catalyst PdL2 (L = t-BuCN) with the C═C bond in EP, followed by the oxidative cyclization/reductive decyclization-assisted C═C double-bond rotation processes resulting in ZP' and regeneration of PdL2. (ii) The origin of the product E/Z selectivity is the second issue. On the basis of the calculated results, it is found that, at the initial stage of the reaction, EP is certainly completely generated, while no ZP' formation occurred. Once E1 is used up, EP immediately acts as the partner of the new catalytic cycle and sluggishly evolves into ZP'. A small amount of generated ZP' would reversibly transform to EP due to the higher barrier involved. (iii) The intrinsic reasons for the regioselectivity are the third issue. The calculated results indicate that the regioselectivity for α-C-H activation is mainly attributed to the stronger electrostatic attraction between the α-C and the metal center.
N-(2-Fluoro-phen-yl)cinnamamide
Acta Crystallogr Sect E Struct Rep Online 2010 Feb 6;66(Pt 3):o533-4.PMID:21580305DOI:10.1107/S1600536810003867.
The title compound, C(15)H(12)FNO, was prepared by the reaction of cinnamoyl chloride with 4-fluoro-aniline and crystallizes with two mol-ecules A and B in the asymmetric unit. The two unique mol-ecules are closely similar and overlay with an r.m.s. deviation of 0.0819 Å. The fluoro-benzene and phenyl rings are inclined to one another at 73.89 (7) and 79.46 (7)°, respectively, in mol-ecules A and B. The amide C-N-C(O)-C portions of the mol-ecules are planar (r.m.s. deviations = 0.035 and 0.028 Å) and are inclined at 45.51 (9) and 47.71 (9), respectively, to the fluoro-benzene rings in mol-ecules A and B. The 2-fluoro-acetamide units and the benzene rings each adopt E configurations with respect to the C=C bonds. In the crystal structure, inter-molecular N-H⋯O hydrogen bonds augmented by weak C-H⋯π inter-actions link mol-ecules into rows in a head-to-tail fashion along a. Additional weak C-H⋯O contacts further stabilize the packing, forming a three-dimensional network stacked down a.
Design, Synthesis, and Fungicidal Activities of Indole-Modified Cinnamamide Derivatives
Chem Biodivers 2023 Jan;20(1):e202200971.PMID:36418220DOI:10.1002/cbdv.202200971.
Dimethomorph is a kind of cinnamamide fungicide with high fungicidal activities for oomycete diseases. The commercially available dimethomorph is a mixture of two isomers, in which (Z)-dimethomorph possessing higher activity and (E)-dimethomorph possessing lower activity. Herein, we reported the design, synthesis and fungicidal activities of a series of novel indole-modified cinnamamide derivatives, which used the indole group to 'fix' the cis-styrene group in (Z)-dimethomorph. The modification of the molecular structure of cinnamamide compounds could be beneficial to improve its practical application performance. Tested the fungicidal activities, it was found that compounds 8j, 9a, 9e, 9i and 9j showed excellent in vivo fungicidal activities (80-100 %) against Pseudoperonospora cubensis at a concentration of 100 mg L-1 , while dimethomorph and flumorph were noneffective. Moreover, parts of synthesized indole-modified cinnamamide derivatives 8 (8a, 8c, 8d and 8j) and 9 (9c and 9j) exhibited the same in vivo fungicidal activities against Phytophthora infestans with dimethomorph or flumorph at a concentration of 50 mg L-1 with 100 % inhibition. The biological assay results indicated that indole-modified cinnamamide derivatives have promising applications in the prevention and treatment of Phytophthora infestans.