77716-14-4

Basic information

• Product Name: Benzyl 4-Amino-1-methylpyrrole-2-carboxylate
• Synonyms: Benzyl 4-Amino-1-methylpyrrole-2-carboxylate
• CAS NO: 77716-14-4
• Molecular Weight: 230.266
• Mol File: 77716-14-4.mol

Chemical Properties

• CAS DataBase Reference: Benzyl 4-Amino-1-methylpyrrole-2-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Benzyl 4-Amino-1-methylpyrrole-2-carboxylate(77716-14-4)
• EPA Substance Registry System: Benzyl 4-Amino-1-methylpyrrole-2-carboxylate(77716-14-4)

Safety Data

• Hazardous Substances Data: 77716-14-4(Hazardous Substances Data)

Upstream product

• 77716-13-3 benzyl 4-<<(tert-butyloxy)carbonyl>amino>-1-methyl-pyrrole-2-carboxylate 
• 6973-60-0 1-Methyl-2-pyrrolecarboxylic acid 
• 37619-24-2 methyl N-methylpyrrole-2-carboxylate 
• 126092-96-4 methyl 4-<<(tert-butyloxy)carbonyl>amino>-1-methyl-pyrrole-2-carboxylate 
• 77716-12-2 Caesium; 4-tert-butoxycarbonylamino-1-methyl-1H-pyrrole-2-carboxylate 
• 2853-29-4 ethyl 1-methyl-4-nitro-1H-pyrrole-2-carboxylate 
• 13138-78-8 1-methyl-4-nitro-pyrrol-2-carboxylic acid 
• 72083-62-6 methyl 4-amino-1-methyl-1H-pyrrole-2-carboxylate 
• 13138-76-6 1-methyl-4-nitropyrrole-2-carboxylic acid methyl ester 
• 77716-11-1 4-[(tert-butoxycarbonyl)amino]-1-methyl-1H-pyrrole-2-carboxylic acid 
• 120095-66-1 benzyl 1-methyl-4-nitropyrrole-2-carboxylate 

Downstream Products

• 132553-01-6 1-Methyl-4-[(1-methyl-4-nitro-1H-pyrrole-2-carbonyl)-amino]-1H-pyrrole-2-carboxylic acid benzyl ester 
• 77716-15-5 benzyl 4-<<<4-<<(tert-butyloxy)carbonyl>amino>-1-methyl-pyrrol-2-yl>carbonyl>amino>-1-methyl-pyrrole-2-carboxylate 
• 85407-15-4 (7-tert-Butoxycarbonylamino-5,10-dioxo-5H,10H-dipyrrolo[1,2-a;1',2'-d]pyrazin-2-yl)-carbamic acid tert-butyl ester 
• 85406-67-3 4-[(4-tert-Butoxycarbonylamino-1H-pyrrole-2-carbonyl)-amino]-1-methyl-1H-pyrrole-2-carboxylic acid benzyl ester 
• 85406-61-7 4-[(4-tert-Butoxycarbonylamino-1-ethyl-1H-pyrrole-2-carbonyl)-amino]-1-methyl-1H-pyrrole-2-carboxylic acid benzyl ester 
• 107164-52-3 benzyl 4-<<<1-(tert-butoxycarbonyl)-4-<(tert-butoxycarbonyl)amino>-pyrrole-2-yl>carbonyl>amino>-1-methylpyrrole-2-carboxylate 
• 158811-72-4 benzyl 4-(3-tert-butoxycarbonylamino-1-methylpyrazole-5-carbamide)-1-methylpyrrole-2-carboxylate 
• 132584-70-4 1-Methyl-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}-1H-pyrrole-2-carboxylic acid benzyl ester 
• 132553-02-7 1-Methyl-4-({1-methyl-4-[(1-methyl-4-nitro-1H-pyrrole-2-carbonyl)-amino]-1H-pyrrole-2-carbonyl}-amino)-1H-pyrrole-2-carboxylic acid benzyl ester 
• 183853-88-5 4-({4-[(4-Amino-1-methyl-1H-pyrrole-2-carbonyl)-amino]-1-methyl-1H-pyrrole-2-carbonyl}-amino)-1-methyl-1H-pyrrole-2-carboxylic acid benzyl ester 
• 6576-51-8 distamycin A hydrochloride 
• 107164-67-0 C₂₃H₂₉N₉O₄*BrH 
• 107164-64-7 4-({4-[(4-Formylamino-1-pentyl-1H-pyrrole-2-carbonyl)-amino]-1H-pyrrole-2-carbonyl}-amino)-1-methyl-1H-pyrrole-2-carboxylic acid benzyl ester 
• 107164-63-6 4-({4-[(1-Butyl-4-formylamino-1H-pyrrole-2-carbonyl)-amino]-1H-pyrrole-2-carbonyl}-amino)-1-methyl-1H-pyrrole-2-carboxylic acid benzyl ester 

Relevant articles and documents

Synthesis and evaluation of a netropsin-proximicin-hybrid library for DNA binding and cytotoxicity

The proximicins A-C (1-3) are novel naturally occurring γ-peptides with a hitherto unknown 2,4-disubstituted furan amino acid as a core structure. They show a moderate cytotoxic activity and induce upregulation of cell cycle regulating proteins (p53 and p21) and lead to cell cycle arrest in G0/G1-phase. Hybrid molecules combining structural motifs of the proximicins and of netropsin (4), a structurally related natural product, seem to have similar effects. Herein we describe the synthesis of a netropsin-proximicin-hybrid library and its evaluation regarding cytotoxicity and minor groove binding activity.

Novel heterocyclic Tro?ger's base derivatives containing N-methylpyrrole units

Novel analogues of Tr?ger's base were prepared regioselectively from 4-amino-N-methylpyrrole carboxylates in good yield. Catalytic hydrogenation of dibenzyl-4,9-methano-1,6-dimethyl-4,5,9,10-tetrahydro-1H,6H-dipyrrolo- [3,2-b:3′,2′-f][1,5]diazocin-2,7-dicarboxylate 2b led to 4,9-methano-1,6-dimethyl-4,5,9,10-tetrahydro-1H,6H-dipyrrolo-[3,2-b: 3′,2′-f][1,5]diazocin-2,7-dicarboxylic acid 3 which was used for the preparation of Tr?ger's base derivatives of natural antibiotics via an amide protocol. The novel heterocyclic Tr?ger's bases were characterized by a variety of spectroscopic techniques and compound 2b by X-ray crystallography. Incorporation of guanidine as the terminal group in the N-methylpyrrole Tr?ger's base skeleton opens the possibility for preparation of water soluble derivatives.

Method for the synthesis of pyrrole and imidazole carboxamides on a solid support

The present invention describes a novel method for the solid phase synthesis of polyamides containing imidazole and pyrrole carboxamides. The polyamides are prepared on a solid support from aromatic carboxylic acids and aromatic amines with high stepwise coupling yields (>99%), providing milligram quantities of highly pure polyamides. The present invention also describes the synthesis of analogs of the natural products Netropsin and Distamycin A, two antiviral antibiotics. The present invention also describes a novel method for the solid phase synthesis of imidazole and pyrrole carboxamide polyamide-oligonucleotide conjugates. This methodology will greatly increase both the complexity and quantity of minor-groove binding polyamides and minor-groove binding polyamide-oligonucleotide conjugates which can be synthesized and tested.

SYNTHESIS OF OLIGO-N-METHYLPYRROLECARBOXAMIDE DERIVATIVES AND THEIR PHOTOCHEMICAL DNA CLEAVING ACTIVITIES

Synthesis of various oligo-N-methylpyrrolecarboxamide derivatives and their DNA cleaving activities under UV-A irradiation were described.

Design, synthesis, DNA binding, and biological activity of a series of DNA minor-groove-binding intercalating drugs

A group of pseudopeptides, molecular combination of the natural antitumor agents distamycin or netropsin and the anilinoacridine chromophore (which is related to the synthetic antileukemic drug amsacrine) has been synthesized. Their DNA binding properties were determined and discussed in terms of their structural differences and in relation to their observed base-dependent binding. Binding data are consistent with a model in which the acridine nucleus occupies an intercalation site and the netropsin or distamycin residue resides in the DNA minor groove. Cytostatic and cytotoxic activities against a murine cell line are reported, as well as significant differences in the inhibition of DNA synthesis.

Novel Efficient Total Synthesis of Antiviral Antibiotic Distamycin A

In connection with an attempt to design a flexible synthesis of analogues of distamycin A (14) for a structure-activity study, by starting from 4-amino>-1-methylpyrrole-2-carboxylic acid (3) and the corresponding formyl derivative (9), the distamycin A precursor 12 was prepared.The versatility of 12 is demonstrated by direct attachment, after activation, of preformed β-aminopropionamidine dihydrobromide to give 14 in fair yield.We conclude that N- and/or ring-substituted derivatives of 3 and 9 may lead to the corresponding analogues of 12 and thus serve as useful precursors, to which the amino amidine or derivatives thereof can be attached.After hydrogenation of the corresponding nitro compound, 3 and 9 were prepared with (tert-butyloxy)carbonyl fluoride and formic anhydride, respectively.Amide bond formations were accomplished with carbodiimides, occasionally via intermediary active esters (8,13).