197705-51-4

Basic information

• Product Name: {4-[(1-Methyl-4-nitro-1H-pyrrole-2-carbonyl)-amino]-phenyl}-carbamic acid tert-butyl ester
• Synonyms: {4-[(1-Methyl-4-nitro-1H-pyrrole-2-carbonyl)-amino]-phenyl}-carbamic acid tert-butyl ester
• CAS NO: 197705-51-4
• Molecular Weight: 360.37
• Mol File: 197705-51-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: {4-[(1-Methyl-4-nitro-1H-pyrrole-2-carbonyl)-amino]-phenyl}-carbamic acid tert-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: {4-[(1-Methyl-4-nitro-1H-pyrrole-2-carbonyl)-amino]-phenyl}-carbamic acid tert-butyl ester(197705-51-4)
• EPA Substance Registry System: {4-[(1-Methyl-4-nitro-1H-pyrrole-2-carbonyl)-amino]-phenyl}-carbamic acid tert-butyl ester(197705-51-4)

Safety Data

• Hazardous Substances Data: 197705-51-4(Hazardous Substances Data)

Upstream product

• 71026-66-9 N-(tert-butoxycarbonyl)-1,4-phenylenediamine 
• 28494-51-1 1-methyl-4-nitro-1H-pyrrole-2-carbonyl chloride 
• 13138-78-8 1-methyl-4-nitro-pyrrol-2-carboxylic acid 

Downstream Products

• 197705-52-5 [4-({1-Methyl-4-[(1-methyl-4-nitro-1H-pyrrole-2-carbonyl)-amino]-1H-pyrrole-2-carbonyl}-amino)-phenyl]-carbamic acid tert-butyl ester 
• 197705-53-6 (4-{[1-Methyl-4-({1-methyl-4-[(1-methyl-4-nitro-1H-pyrrole-2-carbonyl)-amino]-1H-pyrrole-2-carbonyl}-amino)-1H-pyrrole-2-carbonyl]-amino}-phenyl)-carbamic acid tert-butyl ester 
• 197705-54-7 (4-{[4-({4-[(4-{4-[Bis-(2-chloro-ethyl)-amino]-benzoylamino}-1-methyl-1H-pyrrole-2-carbonyl)-amino]-1-methyl-1H-pyrrole-2-carbonyl}-amino)-1-methyl-1H-pyrrole-2-carbonyl]-amino}-phenyl)-carbamic acid tert-butyl ester 

Relevant articles and documents

Structure-activity relationship of a series of C-terminus modified aminoalkyl, diaminoalkyl- and anilino-containing analogues of the benzoic acid mustard distamycin derivative tallimustine: Synthesis, DNA binding and cytotoxicity studies

As part of our investigations into the design of more cytotoxic analogues of the experimental anticancer drug tallimustine, 1, C-terminus modified aminoalkyl-, 2a-c, diaminoalkyl-, 3, and anilino-containing, 4, derivatives have been synthesized. Compounds 2a-c differ by 2, 3, or 4 methylene units in the C-terminus, respectively. Results from an ethidium displacement study on poly(dA-dT), poly(dG-dC), calf thymus DNA and T4 coliphage DNA showed that compounds 2-4 interact in the minor groove of the polynucleotides with a preference for poly(dA-dT) over poly(dG-dC). Compound 4 bound more weakly to the DNAs than 2a-c and 3. Using a CD dilution assay compounds 2a-c and 3 were demonstrated to bind irreversibly to calf thymus DNA. The sequence selectivity by which compounds 2-4 alkylate DNA was demonstrated using a Tag polymerase stop assay. All the compounds alkylated preferentially at the 3'-purine residue in a 5'-TTTTGPu-3' sequence (Pu = A or G). This observed sequence specificity is similar to that of tallimustine and a related compound 5. At an equimolar concentration the aminoalkyl compounds 2a-c (2b > 2a > 2c), and diaminoalkyl compound 3 were more efficient at alkylating these sequences than the anilino compound 4. Following a one hour exposure of human chronic myeloid leukemia K562 cells, compounds 2b and 3 have lower IC50, values (1.64 μM and 3.03 μM, respectively) than tallimustine (5 μM) and similar values to a related compound 5 (2.2 μM) The order of cytotoxicity for all the compounds is 2b > 5 > 3 > 2a > 1 > 2c = 4. These results indicate that the cytotoxicities of these compounds are related to their relative ability to alkylate the consensus DNA binding sequence.