Cinnamamide
(Synonyms: 肉桂酰胺) 目录号 : GC40986
An amide of trans-cinnamic acid
Cas No.:621-79-4
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >95.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Cinnamamide is an amide form of of trans-cinnamic acid and a metabolite of Streptomyces. Cinnamamide exhibits low cytotoxicity against BEL-7402 human hepatoma cells and HT-1080 fibrosarcoma cells and inhibits cell growth (IC50s = 1.94 and 1.29 mM, respectively). In vivo, cinnamamide (40 and 100 mg/kg, i.p.) reduces tumor weight in a mouse model of C26 murine colon carcinoma. Cinnamamide (75 and 150 mg/kg, i.p.) also reduces tumor weight in a mouse model of murine hepatoma 22 by 42% and 49%, respectively, without reducing body weight when delivered one or three days following tumor implantation. When presented with cinnamamide-treated food at a concentration of 0.8% w/w, house and wood mice food consumption is reduced to 32% and 17% of pretreatment levels, respectively, however, wood mouse consumption returns to pretrial levels by day two.
| Cas No. | 621-79-4 | SDF | |
| 别名 | 肉桂酰胺 | ||
| Canonical SMILES | NC(/C=C/C1=CC=CC=C1)=O | ||
| 分子式 | C9H9NO | 分子量 | 147.2 |
| 溶解度 | DMF: 30 mg/ml,DMSO: 30 mg/ml,DMSO:PBS (pH 7.2) (1:4): 0.20 mg/ml,Ethanol: 5 mg/ml | 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 | 6.7935 mL | 33.9674 mL | 67.9348 mL |
| 5 mM | 1.3587 mL | 6.7935 mL | 13.587 mL |
| 10 mM | 0.6793 mL | 3.3967 mL | 6.7935 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。
Cinnamamide: An insight into the pharmacological advances and structure-activity relationships
Eur J Med Chem 2019 Nov 1;181:111561.PMID:31376564DOI:10.1016/j.ejmech.2019.07.064.
The Cinnamamide (cinnamic acid amide and cinnamide) is a privileged scaffold present widely in a number of natural products. The scaffold acts as a useful template for designing and arriving at newly drug-like molecules with potential pharmacological activity. An attempt has been made to review the extensive occurrence of Cinnamamide scaffold in many lead compounds reported for treating various diseases, their binding interactions with the therapeutic targets as well as mechanism of action and their structure-activity relationships. The discoveries of Cinnamamide systems and some examples of unusual cinnamamides having an aromatic, aliphatic, and heterocyclic or other rings condensed to the basic Cinnamamide structure also have been extensively covered in this review.
Cinnamamide Derivatives for Central and Peripheral Nervous System Disorders--A Review of Structure-Activity Relationships
ChemMedChem 2015 Aug;10(8):1302-25.PMID:26083325DOI:10.1002/cmdc.201500153.
The Cinnamamide scaffold has been incorporated in to the structure of numerous organic compounds with therapeutic potential. The scaffold enables multiple interactions, such as hydrophobic, dipolar, and hydrogen bonding, with important molecular targets. Additionally, the scaffold has multiple substitution options providing the opportunity to optimize and modify the pharmacological activity of the derivatives. In particular, Cinnamamide derivatives have exhibited therapeutic potential in animal models of both central and peripheral nervous system disorders. Some have undergone clinical trials and were introduced on to the pharmaceutical market. The diverse activities observed in the nervous system included anticonvulsant, antidepressant, neuroprotective, analgesic, anti-inflammatory, muscle relaxant, and sedative properties. Over the last decade, research has focused on the molecular mechanisms of action of these derivatives, and the data reported in the literature include targeting the γ-aminobutyric acid type A (GABAA ) receptors, N-methyl-D-aspartate (NMDA) receptors, transient receptor potential (TRP) cation channels, voltage-gated potassium channels, histone deacetylases (HDACs), prostanoid receptors, opioid receptors, and histamine H3 receptors. Here, the literature data from reports evaluating cinnamic acid amide derivatives for activity in target-based or phenotypic assays, both in vivo and in vitro, relevant to disorders of the central and peripheral nervous systems are analyzed and structure-activity relationships discussed.
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.
Discovery of cinnamamide-barbiturate hybrids as a novel class of Nrf2 activator against myocardial ischemia/reperfusion injury
Bioorg Chem 2022 Jul;124:105828.PMID:35490584DOI:10.1016/j.bioorg.2022.105828.
Myocardial ischemia/reperfusion (MI/R) has been a challenge for global public health. Activation of nuclear factor erythroid-2-related factor 2 (Nrf2) signaling could attenuate MI/R injury by maintaining cell redox balance and reducing oxidative damage. Cinnamamide derivatives have been proven to be a class of potential Nrf2 activators and cardioprotective agents. The development of novel Cinnamamide derivatives to combat oxidative stress in cardiomyocytes is highly desirable. In this study, twenty-three cinnamamide-barbiturate hybrids were studied. Cell-based assays showed that most of the compounds exhibited excellent protective activity against H2O2-induced oxidative injury in H9c2 cells. Notably, compound 7w, which had the highest activity and low cytotoxicity, was demonstrated to remarkably reduce intracellular ROS accumulation by activating the mRNA expression of Nrf2 and its downstream antioxidant gene HO-1, indicating a novel promising antioxidant and Nrf2 activator. The probable binding mode between protein Keap1 and compound 7w was also studied via molecule docking. Furthermore, we found that the administration of compound 7w could significantly reduce the cardiac infarct size and improve the cardiac function against MI/R injury in rats, as well as decrease cardiac oxidative stress. Taken together, we report, for the first time, that cinnamamide-barbiturate hybrids are a novel class of potential cardioprotective agents. The excellent cardioprotective action of such compounds rely on enhancing the endogenous antioxidative system by upregulating the Nrf2 signaling pathway in vitro and in vivo against MI/R damage. These findings provide a new perspective for designing cinnamamide-barbiturate hybrids as a novel class of Nrf2 activator against cardiovascular diseases.
New benzamide derivatives and their nicotinamide/Cinnamamide analogs as cholinesterase inhibitors
Mol Divers 2022 Apr;26(2):1201-1212.PMID:34165688DOI:10.1007/s11030-021-10249-9.
In this study, a total of 18 new benzamide/ nicotinamide/ Cinnamamide derivative compounds were designed and synthesized for the first time (except B1 and B5) by conventional and microwave irradiation methods. The chemical structures of the synthesized compounds were characterized by 1H NMR, 13C NMR, and HRMS spectra. In vitro acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) inhibition effects of the compounds were evaluated to find out new possible drug candidate molecule/s. According to the inhibition results, the IC50 values of the compounds synthesized were in the range of 10.66-83.03 nM towards AChE, while they were in the range of 32.74-66.68 nM towards BuChE. Tacrine was used as the reference drug and its IC50 values were 20.85 nM and 15.66 nM towards AChE and BuChE, respectively. The most active compounds B4 (IC50: 15.42 nM), N4 (IC50: 12.14 nM), and C4 (IC50: 10.67 nM) in each series towards AChE were docked at the binding site of AChE enzyme to explain the inhibitory activities of each series. On the other hand, the compounds B4, N4, and C4 showed satisfactory pharmacokinetic properties via the prediction of ADME profiles.