Oxindole (Indolin-2-one)
(Synonyms: 2-吲哚酮,Indolin-2-one) 目录号 : GC31140
An aromatic heterocycle and starting material
Cas No.:59-48-3
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.50%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Oxindole is an aromatic heterocycle and starting material in the synthesis of numerous biologically active compounds including, but not limited to, anticancer, antibacterial, and antidiabetic agents, enzyme inhibitors, and channel blockers.1,2
1.Ziarani, G.M., Gholamzadeh, P., Lashgari, N., et al.Oxindole as starting material in organic synthesisARKIVOC2013(1)470-535(2013) 2.Kaur, M., Singh, M., Chadha, N., et al.Oxindole: A chemical prism carrying plethora of therapeutic benefitsEur. J. Med. Chem.123858-894(2016)
| Cas No. | 59-48-3 | SDF | |
| 别名 | 2-吲哚酮,Indolin-2-one | ||
| Canonical SMILES | O=C1NC2=C(C=CC=C2)C1 | ||
| 分子式 | C8H7NO | 分子量 | 133.15 |
| 溶解度 | DMSO : 100 mg/mL (751.03 mM) | 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 | 7.5103 mL | 37.5516 mL | 75.1033 mL |
| 5 mM | 1.5021 mL | 7.5103 mL | 15.0207 mL |
| 10 mM | 0.751 mL | 3.7552 mL | 7.5103 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。
Oxindole and its derivatives: A review on recent progress in biological activities
Biomed Pharmacother.2021 Sep;141:111842.PMID:34174506DOI: 10.1016/j.biopha.2021.111842.
Oxindole has been shown to be a pharmacologically advantageous scaffold having many biological properties that are relevant to medicinal chemistry. The simplicity and widespread occurrence of this scaffold in plant-based alkaloids have further reinforced oxindole's merit in the domain of novel drug discovery. First extracted from Uncaria tomentosa, commonly the known as cat claw's plant which was found abundantly in the Amazon rainforest, molecules with the oxindole moiety have been shown to be common in a wide variety of compounds extracted from plant sources. The role of oxindole as a chemical scaffold for fabricating and designing biological drugs agents can be ascribed to its ability to be modified by a number of chemical groups to generate novel biological functions. This review is aimed at providing a description of the general chemistry based on existing corresponding structure-activity relationships (SARs) and compile all recent developmentary studies on oxindole-derived compounds as a successful pharmaceutical agent. A substantial group of oxindole derivatives are chiefly being tested as anticancer agents, however, a several oxindole derivatives have been shown to possesses antimicrobial, α-glucosidase inhibitory, antiviral, antileishmanial, antitubercular, antioxidative, tyrosinase inhibitory, PAK4 inhibitory, antirheumatoid arthritis and intraocular pressure reducing activities, to name a few. In this review we show the potential value of developing newer oxindole derivatives with an improved range of pharmacological implications as well as identifying drugs possessing oxindole core, that are showing and serving increased efficacy in clinical practice.
Oxindole: A chemical prism carrying plethora of therapeutic benefits
Eur J Med Chem.2016 Nov 10;123:858-894.PMID:27543880DOI: 10.1016/j.ejmech.2016.08.011.
Oxindole has emerged as a valuable scaffold in medicinal chemistry possessing diverse range of pharmacological activities. Its value has further been increased by its natural occurrence as alkaloids in variety of plants. It was first extracted from the cat claw's plant Uncaria tomentosa found in the Amazon rainforest and other tropical areas of South and Central America. Traditionally as well as present emerging therapeutic potential of oxindole nucleus has captured the interest of medicinal chemists to synthesize novel oxindole derivatives. In the present review the authors have integrated its chemistry and synthetic strategies developed after 1945. Also the information of naturally occurring oxindole alkaloids has been incorporated. The detailed pharmacological activities including anti-cancer, anti-HIV, antidiabetic, antibacterial, antioxidant, kinase inhibitory, AChE inhibitory, anti-leishmanial, β3 adrenergic receptor agonistic, phosphatase inhibitory, analgesic, spermicidal, vasopressin antagonists, progesterone antagonists, neuroprotection, and NMDA blocker activities of oxindole derivatives alongwith their SAR has also been discussed in detail. Additionally, information regarding the oxindole derivatives in clinical trials has been incorporated. Thus, this review will provide insights for the synthetic as well as medicinal chemist for the designing and synthesis of novel oxindole derivatives with novel improved range of pharmacological implications.
Novel oxindole compounds inhibit the aggregation of amyloidogenic proteins associated with neurodegenerative diseases
Biochim Biophys Acta Gen Subj.2022 May;1866(5):130114.PMID:35217127DOI: 10.1016/j.bbagen.2022.130114.
Amyloidogenic proteins form aggregates in cells, thereby leading to neurodegenerative disorders, including Alzheimer's and prion's disease, amyotrophic lateral sclerosis (ALS) in humans, and degenerative myelopathy (DM) and cognitive dysfunction in dogs. Hence, many small-molecule compounds have been screened to examine their inhibitory effects on amyloidogenic protein aggregation. However, no effective drug suitable for transition to clinical use has been found. Here we examined several novel oxindole compounds (GIF compounds) for their inhibitory effects on aggregate formation of the canine mutant superoxide dismutase 1 (cSOD1 E40K), a causative mutation resulting in DM, using Thioflavin-T fluorescence. Most GIF compounds inhibited the aggregation of cSOD1 E40K. Among the compounds, GIF-0854-r and GIF-0890-r were most effective. Their inhibitory effects were also observed in cSOD1 E40K-transfected cells. Additionally, GIF-0890-r effectively inhibited the aggregate formation of human SOD1 G93A, a causative mutation of ALS. GIF-0827-r and GIF-0856-r also effectively inhibited aggregate formation of human prion protein (hPrP). Subsequently, the correlation between their inhibitory effects on cSOD1 and hPrP aggregation was shown, indicating GIF compounds inhibited the aggregate formation of multiple amyloidogenic proteins. Conclusively, the novel oxindole compounds (GIF-0827-r, GIF-0854-r, GIF-0856-r, and GIF-0890-r) are proposed as useful therapeutic candidates for amyloidogenic neurodegenerative disorders.
RK-270D and E, Oxindole Derivatives from Streptomyces sp. with Anti-Angiogenic Activity
J Microbiol Biotechnol.2022 Mar 28;32(3):302-306.PMID:35058400DOI: 10.4014/jmb.2110.10039.
A chemical investigation of a culture extract from Streptomyces sp. RK85-270 led to the isolation and characterization of two new oxindoles, RK-270D (1) and E (2). The structures of 1 and 2 were determined by analyzing spectroscopic and spectrometric data from 1D and 2D NMR and High-resolution electrospray ionization mass spectrometry (HRESIMS) experiments. Compound 1 exhibited anti-angiogenic activities against human umbilical vein endothelial cells (HUVECs) without cytotoxicity. Results of Western blot analysis revealed that 1 inhibits VEGF-induced angiogenesis in the HUVECs via VEGFR2/ p38 MAPK-mediated pathway.
Oxindole based oxadiazole hybrid analogs: Novel α-glucosidase inhibitors
Bioorg Chem.2018 Feb;76:273-280.PMID:29223804DOI: 10.1016/j.bioorg.2017.12.001.
Inhibition of α-glucosidase is an effective strategy for controlling post-prandial hyperglycemia in diabetic patients. Beside these α-glucosidase inhibitors has been also used as anti-obesity and anti-viral drugs. Keeping in view the greater importance of α-glucosidase inhibitors here in this study we are presenting oxindole based oxadiazoles hybrid analogs (1-20) synthesis, characterized by different spectroscopic techniques including 1H NMR and EI-MS and their α-glucosidase inhibitory activity. All compounds were found potent inhibitors for the enzyme with IC50 values ranging between 1.25 ± 0.05 and 268.36 ± 4.22 µM when compared with the standard drug acarbose having IC50 value 895.09 ± 2.04 µM. Our study identifies novel series of potent α-glucosidase inhibitors and further investigation on this may led to the lead compounds. A structure activity relationship has been established for all compounds. The interactions of the active compounds and enzyme active site were established with the help of molecular docking studies.