Chapter 11.2, Problem 4ATS

Draw the structure of the following three isomeric amides with chemical formula C,H NO. Amide #1: N-ethylcyclopropanecarboxamide Amide #2: (Z)-3-hexenamide Amide #3: N-methylcyclobutanecarboxamide • Consider E/Z stereochemistry of alkenes. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. • Separate structures with + signs from the drop-down menu. opy aste ChemDoodle (Provious Next Email Instructor Save a

A chemically modified guanidino group is present in cimetidine (Tagamet), a widely prescribed drug for the control of gastric acidity and peptic ulcers. Cimetidine reduces gastric acid secretion by inhibiting the interaction of histamine with gastric H2 receptors. In the development of this drug, a cyano group was added to the substituted guanidino group to alter its basicity. Do you expect this modified guanidino group to be more basic or less basic than the guanidino group of arginine? Explain.

Fats can be either optically active or optically inactive, depending on their structure. Draw the structure of an optically active fat that yields 2 equivalents of stearic acid and 1 equivalent of oleic acid on hydrolysis. Draw the structure of an optically inactive fat that yields the same products.

The addition of a nucleophilic group like a thiol (-SH), or an unprotonated amino group (-NH₂) to an a,ß-unsaturated ketone is important for understanding how NAPQI reacts with glutathione, N-acetylcysteine, or protein amino acid side chains containing -SH or -NH2 groups. In this problem we will add mercaptoethanol to p-benzoquinone. p-Benzoquinone will be a simple model of NAPQI. +H H a single uncharged addition product This reaction will proceed in steps. First the H-S-R will add to the unsaturated ketone to give a charged addition product. Next, a simple proton transfer will form an uncharged adduct in which the 6-membered ring contains one carbonyl and a second enolic hydroxyl. The keto form next will tautomerize to its more stable enol form, and in doing so the 6-membered ring becomes aromatic with 6-π electrons. See page 14 of the lecture notes for Lecture 9 How ADME affects preclinical Drug Design February 24, 2023, where I have shown the mechanism for this addition and give the…

Starting with benzene synthesize the amino acid phenylalanine 1. using the strecker approach 2. by reductive amination

The start drug is Tolbutamide and the product is Chlorpropamide. Which of the following is incorrect? a. the -CH3 groyp is replaced with Cl atom to prevent oxidation of –CH3 group   b. The -CH3 group in Tolbutamidw can be easily oxidized into -CH20H, and then to –CO2H   c. this modification is used to prolong the duration of action of chlorpropamide   d. this modification is achieved by an oxygen enzyme   e. none of the above

During acidosis of a protein, shown below, salt bridges are broken, resulting in denaturation.  Which choice shows the products of alkalosis?

In the mid-1930s a substance was isolated from a fungus that is a parasite of ryes and other grasses. This alkaloid, lysergic acid, has been of great interest to chemists because of its strange, dramatic action on the human mind. Many derivatives of lysergic acid are known, some with medicinal applications. Perhaps the best known derivative of lysergic acid is the potent hallucinogen lysergic acid diethylamide (LSD): మగవా జి N-H LSD (CH25N;O) Like other alkaloids, LSD is a weak base, with Kp = 7.6 × 107. What is the pH of a 0.94 M solution of LSD? pH =

Researchers at Rutgers University have developed biocompatible polymers that degrade into nonsteroidal antiinammatory drugs. For example, the reaction of two equivalents of benzyl salicylate and one equivalent of sebacoyl chloride forms a poly(anhydride ester) called PolyAspirin, which hydrolyzes to salicylic acid (an anti-inammatory agent) and sebacic acid, which is excreted. This technology can perhaps be used for localized drug delivery at specic sites of injury. What is the structure of PolyAspirin?