138730-81-1

Basic information

• Product Name: 5-(tert-butoxycarbonylamino)-1H-indole-2-carboxylic acid
• Synonyms: 5-(tert-butoxycarbonylamino)-1H-indole-2-carboxylic acid;5-[[(1,1-dimethylethoxy)carbonyl]amino]-1H-Indole-2-carboxylic acid
• CAS NO: 138730-81-1
• Molecular Formula: C₁₄H₁₆N₂O₄
• Molecular Weight: 276.28784
• Mol File: 138730-81-1.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5-(tert-butoxycarbonylamino)-1H-indole-2-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(tert-butoxycarbonylamino)-1H-indole-2-carboxylic acid(138730-81-1)
• EPA Substance Registry System: 5-(tert-butoxycarbonylamino)-1H-indole-2-carboxylic acid(138730-81-1)

Safety Data

• Hazardous Substances Data: 138730-81-1(Hazardous Substances Data)

Usage

General Description

The chemical "5-(tert-butoxycarbonylamino)-1H-indole-2-carboxylic acid" is a compound with a complex structure containing an indole ring and a carboxylic acid group. The presence of the tert-butoxycarbonylamino group suggests that it may be used as a protecting group for the indole nitrogen atom, allowing for selective modification of other functional groups in the molecule. 5-(tert-butoxycarbonylamino)-1H-indole-2-carboxylic acid may have potential applications in organic synthesis, medicinal chemistry, or as a building block for the creation of more complex molecules. Its specific properties and potential uses would need to be further investigated through experimental studies.

Upstream product

• 152213-40-6 5-amino-1H-indole-2-carboxylic acid 
• 24424-99-5 di-tert-butyl dicarbonate 
• 138730-80-0 ethyl 5-[(tert-butoxycarbonyl)amino]-1H-indole-2-carboxylate 
• 16732-57-3 5-nitro-indole-2-carboxylic acid ethyl ester 
• 71086-99-2 ethyl 5-amino-1H-indole-2-carboxylate 

Downstream Products

• 1093261-06-3 1,1-dimethylethyl (2-{[({4-chloro-3-[(3-chloro-5-cyanophenyl)oxy]-2-fluorophenyl}methyl)amino]carbonyl}-1H-indol-5-yl)carbamate 
• 1093255-88-9 5-[bis(cyclopropylmethyl)amino]-N-({4-chloro-3-[(3-chloro-5-cyanophenyl)oxy]-2-fluorophenyl}methyl)-1H-indole-2-carboxamide 
• 1093255-87-8 N-({4-chloro-3-[(3-chloro-5-cyanophenyl)oxy]-2-fluorophenyl}methyl)-5-(dimethylamino)-1H-indole-2-carboxamide 
• 1093255-74-3 5-(β-alanylamino)-N-({4-chloro-3-[(3-chloro-5-cyanophenyl)oxy]-2-fluorophenyl}methyl)-1H-indole-2-carboxamide 
• 1190959-60-4 1,1-dimethylethyl {3-[(2-{[({4-chloro-3-[(3-chloro-5-cyanophenyl)oxy]-2-fluorophenyl}methyl)amino]carbonyl}-1H-indol-5-yl)amino]-3-oxopropyl}carbamate 
• 1093255-69-6 5-amino-N-({4-chloro-3-[(3-chloro-5-cyanophenyl)oxy]-2-fluorophenyl}methyl)-1H-indole-2-carboxamide trifluoroacetate 
• 1037798-28-9 C₃₄H₃₂ClN₃O₄ 
• 1037795-58-6 C₃₄H₃₂BrN₃O₄ 
• 199806-27-4 5-({5-[4-((2R,3R,4S,5S,6S)-3,4,5-Triacetoxy-6-methoxycarbonyl-tetrahydro-pyran-2-yloxy)-butyrylamino]-1H-indole-2-carbonyl}-amino)-1H-indole-2-carboxylic acid benzyl ester 
• 199806-24-1 5-amino-1H-indole-2-carboxylic acid benzyl ester 

Relevant articles and documents

DNA alkylation by pyrrole-imidazole seco-CBI conjugates with an indole linker: Sequence-specific DNA alkylation with 10-base-pair recognition through heterodimer formation

The sequence-specific DNA alkylation by conjugates 4 and 5, which consist of N-methylpyrrole (Py)-N-methylimidazole (Im) polyamides and 1-(chloromethyl)-5-hydroxy-1,2-dihydro-3H-benz[e]indole (seco-CBI) linked with an indole linker, was investigated in the absence or presence of partner Py-Im polyamide 6. High-resolution denaturing Polyacrylamide gel electrophoresis revealed that conjugate 4 alkylates DNA at the sequences 5′-(A/T)GCCTA- 3′ through hairpin formation, and alkylates 5′-GGAAA-GAAAA-3′ through an extended binding mode. However, in the presence of partner Py-Im polyamide 6, conjugate 4 alkylates DNA at a completely different sequence, 5′-AGGTTGTCCA-3′. Alkylation of 4 in the presence of 6 was effectively inhibited by a competitor 7. Surface plasmon resonance (SPR) results indicated that conjugate 4 does not bind to 5′-AGGTTGTCCA-3′, whereas 6 binds tightly to this sequence. The results suggest that alkylation proceeds through heterodimer formation, indicating that this is a general way to expand the recognition sequence for DNA alkylation by Py-Im seco-CBI conjugates.

CHEMICAL LINKERS WITH SINGLE AMINO ACIDS AND CONJUGATES THEREOF

The present disclosure provides drug-ligand conjugates that are potent cytotoxins and include a linker between the drug and ligand where the linker has a single amino acid. The disclosure is also directed to compositions containing the drug-ligand conjugates, and to methods of treatment using them.

Synthesis and preliminary cytotoxicity study of glucuronide derivatives of CC-1065 analogues

Glucuronide derivatives of CBI-bearing CC-1065 analogues have been synthesized, and their cytotoxicities tested against U937 leukemia cells. The new compounds show potent antitumor activity in vitro. Compounds 1 and 2, and their corresponding glucuronides