Table of contents

1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 17m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 19m
11. Radical Reactions1h 58m
12. Alcohols, Ethers, Epoxides and Thiols2h 42m
13. Alcohols and Carbonyl Compounds2h 17m
14. Synthetic Techniques1h 26m
15. Analytical Techniques:IR, NMR, Mass Spect7h 3m
16. Conjugated Systems6h 13m
17. Ultraviolet Spectroscopy51m
18. Aromaticity2h 34m
19. Reactions of Aromatics: EAS and Beyond5h 1m
20. Phenols55m
21. Aldehydes and Ketones: Nucleophilic Addition4h 56m
22. Carboxylic Acid Derivatives: NAS2h 51m
23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides1h 10m
24. Enolate Chemistry: Reactions at the Alpha-Carbon1h 53m
25. Condensation Chemistry2h 9m
26. Amines1h 43m
27. Heterocycles2h 0m
28. Carbohydrates5h 53m
29. Amino Acids4h 20m
30. Peptides and Proteins2h 42m
31. Catalysis in Organic Reactions1h 30m
32. Lipids 2h 50m
33. The Organic Chemistry of Metabolic Pathways2h 52m
34. Nucleic Acids1h 32m
35. Transition Metals6h 14m
36. Synthetic Polymers1h 49m

26. Amines

Amine Alkylation

Organic Chemistry

26. Amines

Amine Alkylation

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5:39 minutes

Problem 97b

Textbook Question

Triethylenemelamine (TEM) is an antitumor agent. Its activity is due to its ability to cross-link DNA.
b. Explain why it can cross-link DNA.

Verified step by step guidance

Step 1: Analyze the structure of Triethylenemelamine (TEM). TEM contains three aziridine rings attached to a triazine core. Aziridine rings are three-membered cyclic amines that are highly strained and reactive due to their small ring size.

Step 2: Understand the reactivity of aziridine rings. Aziridine rings are electrophilic and can undergo nucleophilic attack by groups such as amines or thiols present in DNA. This makes them capable of forming covalent bonds with DNA bases.

Step 3: Explain the mechanism of DNA cross-linking. TEM can react with two nucleophilic sites on DNA, such as guanine bases, through its aziridine rings. This leads to the formation of covalent bonds between two DNA strands or within the same strand, effectively cross-linking the DNA.

Step 4: Discuss the biological implications of DNA cross-linking. Cross-linking prevents DNA replication and transcription, which disrupts cellular processes and leads to cell death. This is why TEM is effective as an antitumor agent.

Step 5: Relate the structure to its function. The triazine core of TEM provides a stable scaffold for the reactive aziridine rings, ensuring that the molecule can interact with DNA effectively and exert its antitumor activity.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

DNA Cross-Linking

DNA cross-linking refers to the formation of covalent bonds between DNA strands, which can inhibit DNA replication and transcription. This process is crucial in the mechanism of action for certain antitumor agents, as it disrupts the normal function of DNA, leading to cell death. Cross-linking can occur through various chemical interactions, often involving electrophilic agents that react with nucleophilic sites on the DNA.

Electrophilicity

Electrophilicity is a chemical property of a species that describes its ability to accept electrons. In the context of DNA cross-linking, electrophilic compounds can react with nucleophilic sites on DNA, such as the nitrogen or oxygen atoms in the bases. Triethylenemelamine (TEM) and related compounds can act as electrophiles, facilitating the formation of cross-links that interfere with DNA function.

Antitumor Mechanism of Action

The antitumor mechanism of action involves various strategies that cancer drugs employ to inhibit tumor growth. For agents like TEM, the primary mechanism is through the induction of DNA damage via cross-linking, which prevents cancer cells from successfully replicating their DNA. This leads to cell cycle arrest and apoptosis, making these agents effective in treating certain types of cancer.

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Related Practice

Textbook Question

Rank the amines in each set in order of increasing basicity.

(d)

Textbook Question

Within each structure, rank the indicated nitrogens by increasing basicity.

(f)

Textbook Question

Predict the products of the following reactions.

(d)

Textbook Question

Two widely used pain relievers are aspirin and acetaminophen. Show how you would synthesize these drugs from phenol.

Textbook Question

In Section 10.12, we saw that S-adenosylmethionine (SAM) methylates the nitrogen atom of noradrenaline to form adrenaline, a more potent hormone. If SAM methylates an OH group attached to the benzene ring instead, it completely destroys noradrenaline's activity.

b. Which reaction is more apt to occur, methylation on nitrogen or methylation on oxygen?

Textbook Question

Dimethylamine, (CH₃)₂NH, has a molecular weight of 45 and a boiling point of 7.4 °C. Trimethylamine, (CH₃)₃N, has a higher molecular weight (59) but a lower boiling point (3.5 °C). Explain this apparent discrepancy.

Textbook Question

Rank the following substituted anilines from most basic to least basic:

Textbook Question

Rank each set of compounds in order of increasing boiling points.

(a) triethylamine, di-n-propylamine, n-propyl ether

(b) ethanol, dimethylamine, dimethyl ether

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