Physicochemical Properties
| Molecular Formula | C20H15FN4O |
| Molecular Weight | 346.357707262039 |
| Exact Mass | 346.122 |
| CAS # | 2755847-31-3 |
| PubChem CID | 164886638 |
| Appearance | Typically exists as solid at room temperature |
| LogP | 4.3 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 6 |
| Rotatable Bond Count | 3 |
| Heavy Atom Count | 26 |
| Complexity | 523 |
| Defined Atom Stereocenter Count | 0 |
| InChi Key | NBUUFZOGDLIBJX-UHFFFAOYSA-N |
| InChi Code | InChI=1S/C20H15FN4O/c21-18-19(25-11-5-8-14-6-1-3-9-16(14)25)23-13-24-20(18)26-17-10-4-2-7-15(17)12-22/h1-4,6-7,9-10,13H,5,8,11H2 |
| Chemical Name | 2-[6-(3,4-dihydro-2H-quinolin-1-yl)-5-fluoropyrimidin-4-yl]oxybenzonitrile |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| ln Vitro | With EC50 values of 2.47 μg/mL and 0.71 μg/mL for Sclerotinia sclerotiorum and Staphylococcus apillum, respectively, chitin synthase inhibitor 4 has strong antifungal efficacy [1]. Staphylococcus api and Sclerotinia sclerotiorum are effectively inhibited by chitin synthase inhibitor 4 (50 μg/mL), with respective inhibition rates of 90.3% and 88.7% [1]. The use of chitin synthase inhibitor 4 (1 μg/mL) will cause aberrant hyphal growth, limit hyphal growth, reduce cell content, and cause cell wall disintegration and plasmolysis [1]. Polyantibin D and chitin synthase are both inhibited by chitin synthase inhibitor 4 (50 μM; 3 h), with respective inhibition rates of 63.84% and 68.08% [1]. |
| ln Vivo | Chitin synthase inhibitor 4 (50 μg/mL) shows strong therapeutic and preventive benefits on Sclerotinia sclerotiorum without noticeable phytotoxicity [1]. Chitin synthase inhibitor 4 has modest acute toxicity and no risk of carcinogenesis or mutagenic damage [1]. |
| Animal Protocol |
Animal/Disease Models: Salmonella typhimurium in rats [1] Doses: According to the acute oral toxicity of chemicals - Acute toxicity classification method Route of Administration: po (oral gavage) Experimental Results: According to the toxicity classification standard, the acute toxicity is 3.58, carcinogenic toxicity, mutagenic toxicity is negative. |
| References | [1]. Zhang X, et al. Synthesis, Antifungal Activity, and 3D-QASR of Novel 1,2,3,4-Tetrahydroquinoline Derivatives Containing a Pyrimidine Ether Scaffold as Chitin Synthase Inhibitors. J Agric Food Chem. 2022 Jul 21. |
Solubility Data
| Solubility (In Vitro) | DMSO : ~100 mg/mL (~288.72 mM) |
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.8872 mL | 14.4358 mL | 28.8717 mL | |
| 5 mM | 0.5774 mL | 2.8872 mL | 5.7743 mL | |
| 10 mM | 0.2887 mL | 1.4436 mL | 2.8872 mL |