Is imidazole nucleophilic or electrophilic?
Nitrogen is a better electron donor than carbon and thus is more nucleophilic. Imidazole is an N-nucleophile.
Which is imidazole antifungal?
Ketoconazole is an imidazole broad-spectrum antifungal agent; it inhibits the synthesis of ergosterol, causing cellular components to leak, resulting in death of fungal cells.
Do you expect imidazole to be aromatic?
2.2 Imidazole The imidazole ring is aromatic. Both N atoms are sp2 hybridized.
Which is more basic imidazole or pyridine?
One resembles pyrrole and is not basic. The second nitrogen is structurally similar to the nitrogen atom of pyridine. However, imidazole is about 100 times more basic than pyridine. The increased basicity results from resonance stabilization of the charge to both nitrogen atoms.
What is the major side effect of amphotericin B?
SIDE EFFECTS: Fever, shaking, chills, flushing, loss of appetite, dizziness, nausea, vomiting, headache, shortness of breath, or fast breathing may occur 1 to 3 hours after the infusion is started.
Which class of antifungal drugs does inhibiting squalene Epoxidase?
allylamines
The allylamines are a new class of antifungal drugs that inhibit ergosterol synthesis at the level of squalene epoxidase.
What is the mechanism of action of antifungal drug?
The azole antifungal drugs act by inhibiting the synthesis of the sterol components of the fungal membrane. Azoles are predominantly fungistatic. They inhibit C-14 α-demethylase (a cytochrome P450 [CYP450] enzyme), thereby blocking the demethylation of lanosterol to ergosterol, the principal sterol of fungal membranes.
Which of the following is an antifungal drug that acts by inhibiting fungal DNA synthesis?
Antimetabolite Antifungal Drugs 5-Fluorocytosine acts as an inhibitor of both DNA and RNA synthesis via the intracytoplasmic conversion of 5-fluorocytosine to 5-fluorouracil.
Why do we use imidazole in protein purification?
Imidazole is utilized as a competitive agent for elution of histidine-tagged proteins. In addition, imidazole can be added in low concentrations in the sample and binding buffer in order to reduce the binding of contaminant proteins, and thus increase the final purity.
Why imidazole is a weak base?
In the case of imidazole, the lone pair on nitrogen that gets protonated is not part of the pi-system so when it gets protonated, it is still aromatic. So, imidazole is more basic than pyrrole. The smaller the pKb the stronger the base. So, the prediction and the numbers match and imidazole is more basic.
Why is the imidazole ring more prone to nucleophilic substitution reaction?
While the imidazole ring is rather susceptible to electrophilic attack on an annular carbon, it is much less likely to become involved in nucleophilic substitution reaction unless there is a strongly electron withdrawing substituent’s elsewhere in the ring. In the absence of such activation the position most prone to nucleophilic attack is C-2.
What is the electrophilic and nucleophilic attack of benzimidazole at N-3?
These predict electrophilic attack in imidazole at N-3 or any ring carbon atom, nucleophilic attack at C-2 or C-1 and also the amphoteric nature of the molecule. In Benzimidazole the nucleophilic attack is predicted at C-2.
What is the overall reactivity of imidazoles and benzimidazole?
The overall reactivity of imidazoles and Benzimidazole is referred from sets of resonance structure in which the dipolar contributors have finite importance. These predict electrophilic attack in imidazole at N-3 or any ring carbon atom, nucleophilic attack at C-2 or C-1 and also the amphoteric nature of the molecule.
Can imidazole be used as an electrophilic reagent?
Imidazole can be considered as having properties similar to both pyrrole and pyridine. The electrophilic reagent would attack the unshared electron pair on N-3, but not that on the ‘pyrrole’ nitrogen since it is the part of thearomatic sextet.