864076-02-8

Basic information

• Product Name: methyl 4-(4-((tert-butoxycarbonyl)amino)phenyl)-1-methyl-1H-pyrrole-2-carboxylate
• Synonyms: methyl 4-(4-((tert-butoxycarbonyl)amino)phenyl)-1-methyl-1H-pyrrole-2-carboxylate
• CAS NO: 864076-02-8
• Molecular Weight: 330.384
• Mol File: 864076-02-8.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: methyl 4-(4-((tert-butoxycarbonyl)amino)phenyl)-1-methyl-1H-pyrrole-2-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 4-(4-((tert-butoxycarbonyl)amino)phenyl)-1-methyl-1H-pyrrole-2-carboxylate(864076-02-8)
• EPA Substance Registry System: methyl 4-(4-((tert-butoxycarbonyl)amino)phenyl)-1-methyl-1H-pyrrole-2-carboxylate(864076-02-8)

Safety Data

• Hazardous Substances Data: 864076-02-8(Hazardous Substances Data)

Upstream product

• 1196-90-3 4-bromo-1-methyl-1H-pyrrole-2-carboxylic acid methyl ester 
• 380430-49-9 [4-(tert-butoxycarbonylamino)phenyl]boronic acid 
• 96-54-8 N-Methylpyrrole 
• 184643-69-4 1-(4-bromo-1-methyl-1H-pyrrol-2-yl)-2,2,2-trichloroethan-1-one 
• 330793-01-6 (4-tert-butoxycarbonylaminophenyl)boronic acid pinacol ester 

Downstream Products

• 864076-03-9 4-(4-((tert-butoxycarbonyl)amino)phenyl)-1-methyl-1H-pyrrole-2-carboxylic acid 
• 1428306-05-1 methyl 4-[[4-[[4-(4-aminophenyl)-1-methyl-pyrrole-2-carbonyl]amino]-1-methyl-imidazole-2-carbonyl]amino]-1-methyl-pyrrole-2-carboxylate 
• 1428306-03-9 C₂₉H₃₃N₇O₆ 
• 1428306-01-7 C₂₂H₂₅N₅O₅ 
• 1428306-00-6 C₂₃H₂₆N₄O₅ 
• 1428305-97-8 C₂₃H₂₇N₅O₅ 
• 1383714-47-3 (S)-methyl 4-(4-(4-(4-((7-methoxy-5-oxo-2,3,5,11a-tetrahydro-1H-pyrrolo[2,1-c][1,4]benzodiazepin-8-yl)oxy)butanamido)-1-methyl-1H-imidazole-2-carboxamido)phenyl)-1-methyl-1H-pyrrole-2-carboxylate 
• 1383714-46-2 methyl (S)-4-(4-(4-(4-((7-methoxy-5-oxo-2,3,5,11a-tetrahydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-8-yl)oxy)butanamido)-1-methyl-1H-pyrrole-2-carboxamido)phenyl)-1-methyl-1H-pyrrole-2-carboxylate 
• 1383714-45-1 (S)-methyl 4-(4-(4-(4-(4-((7-methoxy-5-oxo-2,3,5,11a-tetrahydro-1H-pyrrolo[2,1-c][1,4]benzodiazepin-8-yl)oxy)butanamido)phenyl)-1-methyl-1H-pyrrole-2-carboxamido)-1-methyl-1H-pyrrole-2-carboxamido)-1-methyl-1H-pyrrole-2-carboxylate 
• 1428305-86-5 (S)-methyl 4-(4-(4-(4-((7-methoxy-5-oxo-2,3,5,11a-tetrahydro-1H-pyrrolo[2,1-c][1,4]benzodiazepin-8-yl)oxy)butanamido)phenyl)-1-methyl-1H-pyrrole-2-carboxamido)-1-methyl-1H-pyrrole-2-carboxylate 
• 1428305-85-4 (S)-methyl 4-(4-(4-(4-(4-((7-methoxy-5-oxo-2,3,5,11a-tetrahydro-1H-pyrrolo[2,1-c][1,4]benzodiazepin-8-yl)oxy)butanamido)phenyl)-1-methyl-1H-pyrrole-2-carboxamido)phenyl)-1-methyl-1H-pyrrole-2-carboxylate 
• 1428305-84-3 (S)-methyl 4-(4-(4-((7-methoxy-5-oxo-2,3,5,11a-tetrahydro-1Hpyrrolo[2,1-c][1,4]benzodiazepin-8-yl)oxy)butanamido)phenyl)-1-methyl-1H-pyrrole-2-carboxylate 

Relevant articles and documents

New Broad-Spectrum Antibiotics Containing a Pyrrolobenzodiazepine Ring with Activity against Multidrug-Resistant Gram-Negative Bacteria

It is urgent to find new antibiotic classes with activity against multidrug-resistant (MDR) Gram-negative pathogens as the pipeline of antibiotics is essentially empty. Modified pyrrolobenzodiazepines with a C8-linked aliphatic heterocycle provide a new class of broad-spectrum antibacterial agents with activity against MDR Gram-negative bacteria, including WHO priority pathogens. The structure-activity relationship established that the third ring was particularly important for Gram-negative activity. Minimum inhibitory concentrations for the lead compounds ranged from 0.125 to 2 mg/L for MDR Gram-negative, excluding Pseudomonas aeruginosa, and between 0.03 and 1 mg/L for MDR Gram-positive species. The lead compounds were rapidly bactericidal with >5 log reduction in viable count within 4 h for Acinetobacter baumannii and Klebsiella pneumoniae. The lead compound inhibited DNA gyrase in gel-based assays, with an IC50 of 3.16 ± 1.36 mg/L. This study provides a new chemical scaffold for developing novel broad-spectrum antibiotics which can help replenish the pipeline of antibiotics.

BENZODIAZEPINE DERIVATIVES

The invention relates to novel benzodiazepine derivatives with antiproliferative activity and more specifically to novel benzodiazepine compounds of formulae (I), (II) and (III). The invention also provides conjugates of the benzodiazepine compounds linked to a cell-binding agent. The invention further provides compositions and methods useful for inhibiting abnormal cell growth or treating a proliferative disorder in a mammal using the compounds or conjugates of the invention.

GC-Targeted C8-linked pyrrolobenzodiazepine-biaryl conjugates with femtomolar in vitro cytotoxicity and in vivo antitumor activity in mouse models

DNA binding 4-(1-methyl-1H-pyrrol-3-yl)benzenamine (MPB) building blocks have been developed that span two DNA base pairs with a strong preference for GC-rich DNA. They have been conjugated to a pyrrolo[2,1-c][1,4]benzodiazepine (PBD) molecule to produce