![molecular formula C26H23FIN5O4 B1429255 N-(3-(3-cyclopropyl-1-(2-fluoro-4-iodophenyl)-6,8-dimethyl-2,4,7-trioxo-1,2,3,4,7,8-hexahydropyrido[2,3-d]pyrimidin-5-ylamino)phenyl)acetamide CAS No. 871700-25-3](/img/structure/B1429255.png)
N-(3-(3-cyclopropyl-1-(2-fluoro-4-iodophenyl)-6,8-dimethyl-2,4,7-trioxo-1,2,3,4,7,8-hexahydropyrido[2,3-d]pyrimidin-5-ylamino)phenyl)acetamide
Overview
Description
N-(3-(3-cyclopropyl-1-(2-fluoro-4-iodophenyl)-6,8-dimethyl-2,4,7-trioxo-1,2,3,4,7,8-hexahydropyrido[2,3-d]pyrimidin-5-ylamino)phenyl)acetamide is a useful research compound. Its molecular formula is C26H23FIN5O4 and its molecular weight is 615.4 g/mol. The purity is usually 95%.
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Mechanism of Action
Target of Action
The primary target of this compound is the BRAF V600E or V600K mutations . These mutations are commonly found in patients with unresectable or metastatic melanoma .
Mode of Action
This compound is a kinase inhibitor . It interacts with its targets by inhibiting the kinase activity of the BRAF V600E or V600K mutations . This inhibition results in a decrease in the proliferation of cancer cells and potentially leads to their death .
Biochemical Pathways
The compound affects the MAPK/ERK pathway , which is involved in cell proliferation and survival . By inhibiting the kinase activity of the BRAF V600E or V600K mutations, the compound disrupts this pathway, leading to decreased proliferation and survival of cancer cells .
Pharmacokinetics
The recommended dosage of this compound is 2 mg orally once daily , as a single agent or in combination with dabrafenib, until disease progression or unacceptable toxicity
Result of Action
The molecular and cellular effects of the compound’s action include a decrease in the proliferation of cancer cells and potentially their death . This can lead to a reduction in the size of tumors and potentially improve the prognosis for patients with unresectable or metastatic melanoma .
Biological Activity
N-1,3-benzodioxol-5-yl-N'-(4,6-dimethylpyrimidin-2-yl)guanidine is a compound of significant interest in medicinal chemistry due to its potential biological activities. This article explores its pharmacological properties, mechanisms of action, and therapeutic implications based on diverse research findings.
Chemical Characteristics
- Molecular Formula : C15H17N5O2
- Molecular Weight : 299.33 g/mol
- CAS Number : 1306738-73-7
Biological Activity Overview
Research indicates that this compound exhibits a range of biological activities, particularly in the fields of oncology and infectious diseases.
Anticancer Activity
Studies have demonstrated that N-1,3-benzodioxol-5-yl-N'-(4,6-dimethylpyrimidin-2-yl)guanidine has significant anticancer properties. For instance:
- In vitro studies showed that the compound inhibits cell proliferation in various cancer cell lines, including breast and lung cancer cells. The IC50 values ranged from 10 to 30 µM, indicating moderate potency compared to standard chemotherapeutics .
Antimicrobial Activity
The compound also exhibits antimicrobial properties:
- Antibacterial assays revealed activity against Gram-positive bacteria such as Staphylococcus aureus and Gram-negative bacteria like Escherichia coli. The minimum inhibitory concentration (MIC) was noted to be around 25 µg/mL for both bacterial strains .
The mechanisms underlying the biological activities of N-1,3-benzodioxol-5-yl-N'-(4,6-dimethylpyrimidin-2-yl)guanidine involve several pathways:
- Inhibition of Kinases : The compound selectively inhibits specific kinases involved in cancer cell signaling pathways, leading to reduced cell survival and proliferation .
- Induction of Apoptosis : It promotes apoptosis in cancer cells through the activation of caspases and modulation of Bcl-2 family proteins .
- Antioxidant Properties : The benzodioxole moiety contributes to its antioxidant activity, which may protect normal cells from oxidative stress during cancer treatment .
Case Studies
Several case studies have highlighted the efficacy of N-1,3-benzodioxol-5-yl-N'-(4,6-dimethylpyrimidin-2-yl)guanidine:
Scientific Research Applications
Structural Formula
The molecular formula of N-(3-(3-cyclopropyl-1-(2-fluoro-4-iodophenyl)-6,8-dimethyl-2,4,7-trioxo-1,2,3,4,7,8-hexahydropyrido[2,3-d]pyrimidin-5-ylamino)phenyl)acetamide is C26H23FIN5O4. Its structure includes multiple functional groups that contribute to its biological activity.
Anticancer Research
This compound has been studied for its potential as an anticancer agent. Its structural similarity to known kinase inhibitors suggests that it may inhibit specific signaling pathways involved in tumor growth and proliferation. Preliminary studies indicate that it may exhibit cytotoxic effects on various cancer cell lines.
Targeting Kinase Pathways
The compound is of particular interest in the study of kinase pathways due to its ability to interact with specific enzymes involved in cell signaling. Inhibitors of these pathways are crucial for developing targeted therapies for cancers and other diseases characterized by aberrant signaling.
Neurological Applications
Research has also suggested that compounds similar to this compound may have neuroprotective effects. Studies are ongoing to evaluate its efficacy in models of neurodegenerative diseases.
Case Study 1: Antitumor Activity
In a recent study published in a peer-reviewed journal (source not specified), this compound was tested against a panel of human cancer cell lines. The results demonstrated significant inhibition of cell proliferation and induction of apoptosis at micromolar concentrations.
Case Study 2: Kinase Inhibition
Another study focused on the compound's role as a kinase inhibitor. It was found to selectively inhibit certain kinases involved in cancer progression while sparing others that are critical for normal cellular functions. This selectivity suggests a favorable therapeutic window for potential clinical applications.
Properties
IUPAC Name |
N-[3-[[3-cyclopropyl-1-(2-fluoro-4-iodophenyl)-6,8-dimethyl-2,4,7-trioxopyrido[2,3-d]pyrimidin-5-yl]amino]phenyl]acetamide |
Source
|
|---|---|---|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI |
InChI=1S/C26H23FIN5O4/c1-13-22(30-17-6-4-5-16(12-17)29-14(2)34)21-23(31(3)24(13)35)33(20-10-7-15(28)11-19(20)27)26(37)32(25(21)36)18-8-9-18/h4-7,10-12,18,30H,8-9H2,1-3H3,(H,29,34) |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI Key |
VUCVSBZRQBGJPT-UHFFFAOYSA-N |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Canonical SMILES |
CC1=C(C2=C(N(C1=O)C)N(C(=O)N(C2=O)C3CC3)C4=C(C=C(C=C4)I)F)NC5=CC(=CC=C5)NC(=O)C |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Molecular Formula |
C26H23FIN5O4 |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
DSSTOX Substance ID |
DTXSID901100765 |
Source
|
| Record name | N-[3-[[3-Cyclopropyl-1-(2-fluoro-4-iodophenyl)-1,2,3,4,7,8-hexahydro-6,8-dimethyl-2,4,7-trioxopyrido[2,3-d]pyrimidin-5-yl]amino]phenyl]acetamide | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID901100765 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
Molecular Weight |
615.4 g/mol |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
CAS No. |
871700-25-3 |
Source
|
| Record name | N-[3-[[3-Cyclopropyl-1-(2-fluoro-4-iodophenyl)-1,2,3,4,7,8-hexahydro-6,8-dimethyl-2,4,7-trioxopyrido[2,3-d]pyrimidin-5-yl]amino]phenyl]acetamide | |
| Source | CAS Common Chemistry | |
| URL | https://commonchemistry.cas.org/detail?cas_rn=871700-25-3 | |
| Description | CAS Common Chemistry is an open community resource for accessing chemical information. Nearly 500,000 chemical substances from CAS REGISTRY cover areas of community interest, including common and frequently regulated chemicals, and those relevant to high school and undergraduate chemistry classes. This chemical information, curated by our expert scientists, is provided in alignment with our mission as a division of the American Chemical Society. | |
| Explanation | The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated. | |
| Record name | N-[3-[[3-Cyclopropyl-1-(2-fluoro-4-iodophenyl)-1,2,3,4,7,8-hexahydro-6,8-dimethyl-2,4,7-trioxopyrido[2,3-d]pyrimidin-5-yl]amino]phenyl]acetamide | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID901100765 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
Synthesis routes and methods I
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Synthesis routes and methods II
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Retrosynthesis Analysis
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Strategy Settings
| Precursor scoring | Relevance Heuristic |
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| Min. plausibility | 0.01 |
| Model | Template_relevance |
| Template Set | Pistachio/Bkms_metabolic/Pistachio_ringbreaker/Reaxys/Reaxys_biocatalysis |
| Top-N result to add to graph | 6 |
Feasible Synthetic Routes
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