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1. Cyclophosphamide is a chemotherapy medication used to treat various types of cancers (i.e. lymphoma, leukemia, and breast cancer). It belongs to a group of cytotoxic alkylating agents known as Nitrogen mustards. The activity of these drugs is attributed to the chloroethylamine groups. NH Cl R R Cyclophosphamide chloroethylamine In this exercise, you will explore the mechanism responsible for the cytotoxic activity of Nitrogen mustards and how it is possible to tune their activity (therefore their toxicity) by modifying their chemical structure. 1.5 Draw the curved arrows to complete the reaction mechanism of the following reaction. Start with the intramolecular reaction of chloroethylamine and then react the cyclic product with the primary amine. R. R Cl + R'-NH2 1.6 The chloroethylamine has two methylene groups [(CH2)2] between the nitrogen and the halide leaving group. Predict how the reactivity of the molecule will be affected by inserting a third methylene group [(CH2)3]. Explain why. R R. 'N' R N R 1.7 Now that you have figured out the reaction mechanism, let's explore the action mechanism of the following drug. Notice that this molecule is composed of two chloroethylamine groups and therefore can react with two different nucleophiles. Complete the following reaction mechanism. R'-NH2 R-N + R"-NH2 The above reaction is responsible for the activity of the drug. Because of its ability to react with two nucleophiles, the drug can create a bridge between two biologically active molecules and disrupt their activity. This process is known as 'cross-linking'. For example, it can react with two DNA strands and prevent their separation during replication. This will cause cytotoxicity and cell death. 1.8 Draw a scheme/cartoon to represent the general idea of chemical cross-linking. 1.9 The reactivity of nitrogen mustards can be tuned by changing the chemical structure. Compare the reactivity of the two molecules below. Which nitrogen is more nucleophilic? Why? Draw a resonance structure to support your reasoning.

1. Cyclophosphamide is a chemotherapy medication used to treat various types of cancers (i.e. lymphoma, leukemia, and breast cancer). It belongs to a group of cytotoxic alkylating agents known as Nitrogen mustards. The activity of these drugs is attributed to the chloroethylamine groups. NH Cl R R Cyclophosphamide chloroethylamine In this exercise, you will explore the mechanism responsible for the cytotoxic activity of Nitrogen mustards and how it is possible to tune their activity (therefore their toxicity) by modifying their chemical structure. 1.5 Draw the curved arrows to complete the reaction mechanism of the following reaction. Start with the intramolecular reaction of chloroethylamine and then react the cyclic product with the primary amine. R. R Cl + R'-NH2 1.6 The chloroethylamine has two methylene groups [(CH2)2] between the nitrogen and the halide leaving group. Predict how the reactivity of the molecule will be affected by inserting a third methylene group [(CH2)3]. Explain why. R R. 'N' R N R 1.7 Now that you have figured out the reaction mechanism, let's explore the action mechanism of the following drug. Notice that this molecule is composed of two chloroethylamine groups and therefore can react with two different nucleophiles. Complete the following reaction mechanism. R'-NH2 R-N + R"-NH2 The above reaction is responsible for the activity of the drug. Because of its ability to react with two nucleophiles, the drug can create a bridge between two biologically active molecules and disrupt their activity. This process is known as 'cross-linking'. For example, it can react with two DNA strands and prevent their separation during replication. This will cause cytotoxicity and cell death. 1.8 Draw a scheme/cartoon to represent the general idea of chemical cross-linking. 1.9 The reactivity of nitrogen mustards can be tuned by changing the chemical structure. Compare the reactivity of the two molecules below. Which nitrogen is more nucleophilic? Why? Draw a resonance structure to support your reasoning.

Chemistry
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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1. Cyclophosphamide is a chemotherapy medication used to treat various types of cancers (i.e. lymphoma, leukemia, and breast cancer). It belongs to a group of cytotoxic alkylating agents known as Nitrogen mustards. The activity of these drugs is attributed to the chloroethylamine groups. NH Cl R R Cyclophosphamide chloroethylamine In this exercise, you will explore the mechanism responsible for the cytotoxic activity of Nitrogen mustards and how it is possible to tune their activity (therefore their toxicity) by modifying their chemical structure.
Transcribed Image Text:1. Cyclophosphamide is a chemotherapy medication used to treat various types of cancers (i.e. lymphoma, leukemia, and breast cancer). It belongs to a group of cytotoxic alkylating agents known as Nitrogen mustards. The activity of these drugs is attributed to the chloroethylamine groups. NH Cl R R Cyclophosphamide chloroethylamine In this exercise, you will explore the mechanism responsible for the cytotoxic activity of Nitrogen mustards and how it is possible to tune their activity (therefore their toxicity) by modifying their chemical structure.
1.5 Draw the curved arrows to complete the reaction mechanism of the following reaction. Start with the intramolecular reaction of chloroethylamine and then react the cyclic product with the primary amine. R. R Cl + R'-NH2 1.6 The chloroethylamine has two methylene groups [(CH2)2] between the nitrogen and the halide leaving group. Predict how the reactivity of the molecule will be affected by inserting a third methylene group [(CH2)3]. Explain why. R R. 'N' R N R 1.7 Now that you have figured out the reaction mechanism, let's explore the action mechanism of the following drug. Notice that this molecule is composed of two chloroethylamine groups and therefore can react with two different nucleophiles. Complete the following reaction mechanism. R'-NH2 R-N + R"-NH2 The above reaction is responsible for the activity of the drug. Because of its ability to react with two nucleophiles, the drug can create a bridge between two biologically active molecules and disrupt their activity. This process is known as 'cross-linking'. For example, it can react with two DNA strands and prevent their separation during replication. This will cause cytotoxicity and cell death. 1.8 Draw a scheme/cartoon to represent the general idea of chemical cross-linking. 1.9 The reactivity of nitrogen mustards can be tuned by changing the chemical structure. Compare the reactivity of the two molecules below. Which nitrogen is more nucleophilic? Why? Draw a resonance structure to support your reasoning.
Transcribed Image Text:1.5 Draw the curved arrows to complete the reaction mechanism of the following reaction. Start with the intramolecular reaction of chloroethylamine and then react the cyclic product with the primary amine. R. R Cl + R'-NH2 1.6 The chloroethylamine has two methylene groups [(CH2)2] between the nitrogen and the halide leaving group. Predict how the reactivity of the molecule will be affected by inserting a third methylene group [(CH2)3]. Explain why. R R. 'N' R N R 1.7 Now that you have figured out the reaction mechanism, let's explore the action mechanism of the following drug. Notice that this molecule is composed of two chloroethylamine groups and therefore can react with two different nucleophiles. Complete the following reaction mechanism. R'-NH2 R-N + R"-NH2 The above reaction is responsible for the activity of the drug. Because of its ability to react with two nucleophiles, the drug can create a bridge between two biologically active molecules and disrupt their activity. This process is known as 'cross-linking'. For example, it can react with two DNA strands and prevent their separation during replication. This will cause cytotoxicity and cell death. 1.8 Draw a scheme/cartoon to represent the general idea of chemical cross-linking. 1.9 The reactivity of nitrogen mustards can be tuned by changing the chemical structure. Compare the reactivity of the two molecules below. Which nitrogen is more nucleophilic? Why? Draw a resonance structure to support your reasoning.
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