122745-40-8

Basic information

• Product Name: 3H-Benz[e]indole-3-carboxylic acid, 1-(chloromethyl)-1,2-dihydro-5-(phenylmethoxy)-, 1,1-dimethylethyl ester
• CAS NO: 122745-40-8
• Molecular Formula: C25H26ClNO3
• Molecular Weight: 423.939
• Mol File: 122745-40-8.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 3H-Benz[e]indole-3-carboxylic acid, 1-(chloromethyl)-1,2-dihydro-5-(phenylmethoxy)-, 1,1-dimethylethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 3H-Benz[e]indole-3-carboxylic acid, 1-(chloromethyl)-1,2-dihydro-5-(phenylmethoxy)-, 1,1-dimethylethyl ester(122745-40-8)
• EPA Substance Registry System: 3H-Benz[e]indole-3-carboxylic acid, 1-(chloromethyl)-1,2-dihydro-5-(phenylmethoxy)-, 1,1-dimethylethyl ester(122745-40-8)

Safety Data

• Hazardous Substances Data: 122745-40-8(Hazardous Substances Data)

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 161646-55-5 5-(Benzyloxy)-3-(tert-butyloxycarbonyl)-1-<<(2',2',6',6'-tetramethylpiperidino)oxy>methyl>-1,2-dihydro-3H-benzindole 
• 161646-54-4 2-<amino>-4-(benzyloxy)-1-iodonaphthalene 
• 139975-98-7 tert-butyl-(4-hydroxynaphthalen-2-yl)carbamate 
• 501440-80-8 3-(N-tert-butyloxycarbonyl)amino-1-O-(tertbutyloxycarbonyl)-1-naphthol 
• 2764-95-6 4-methoxy-2-naphthylamine 
• 227084-59-5 (E/Z)-tert-butyl 4-(benzyloxy)-1-iodonaphthalene-2-yl(3-chloroallyl)carbamate 
• 100-39-0 benzyl bromide 
• 13802-40-9 1-Methoxy-3-nitronaphthalene 
• 19256-80-5 3-Nitro-1-naphthol 
• 122745-45-3 N-(tert-butyloxycarbonyl)-N-(2-propynyl)-4-(benzyloxy)-1-bromo-2-naphthylamine 
• 122745-38-4 5-(benzyloxy)-3-(tert-butyloxycarbonyl)-1-methylidene-1,2-dihydro-3H-benzindole 
• 122745-37-3 2-((tert-Butyloxycarbonyl)amino)-4-(benzyloxy)-1-bromonaphthalene 
• 122745-36-2 N-(tert-butyloxycarbonyl)-4-(benzyloxy)-2-naphthylamine 

Downstream Products

• 122745-34-0 (+/-)-CBI-CDPI2 
• 945864-24-4 5-benzyloxy-3-[(5-(2-(N,N-dimethylamino)acetylamino)indol-2-yl)carbonyl]-1-(10-chloromethyl)-1,2-dihydro-3H-benz[e]indole 
• 128300-11-8 5-(benzyloxy)-3-(tert-butyloxycarbonyl)-1-(chloromethyl)-1,2-dihydro-3H-benzindole 
• 244154-66-3 tert-butyl (S)-1-(chloromethyl)-5-((4-methylpiperazine-1-carbonyl)oxy)-1,2-dihydro-3H-benzo[e]indole-3-carboxylate 
• 122745-41-9 tert-butyl (1S)-1-(chloromethyl)-5-hydroxy-1,2-dihydro-3H-benzo[e]indole-3-carboxylate 
• 130008-89-8 3-(tert-butyloxycarbonyl)-1-(chloromethyl)-5-hydroxy-1,2-dihydro-3H-benzindole 

Relevant articles and documents

Controlling the radical 5-exo-trig cyclization, and selective synthesis of seco-iso-cyclopropylfurano[e]indoline (seco-iso-CFI) and seco- cyclopropylthiophene[e]indoline (seco-CTI) DNA alkylating subunit of the duocarmycins

The free radical cyclization of benzofuran bromo-allylic chloride 6 in toluene produced an unpredicted mixture of 6-benzyloxy-N-t-Boc-3-(chloromethyl) furano[e]indoline (1) and 7-benzyloxy-N-Boc-3-(chloromethyl)furano[f]quinoline (2). DFT calculations indicated that the indoline radical (6B), formed from 5-exo-trig closure of intermediate 6A, was less polar than the corresponding quinoline radical (6C). Based on this result, we report herein that cyclization of chlorides 6-8 in a polar aromatic solvent consistently and exclusively produced the indoline product in good yield (74-83%).

CHEMICAL LINKERS AND CLEAVABLE SUBSTRATES AND CONJUGATES THEREOF

The present disclosure provides drug-ligand conjugates and drug-cleavable substrate conjugates that are potent cytotoxins. The disclosure is also directed to compositions containing the drug-ligand conjugates, and to methods of treatment using them.

Synthesis of CC-1065 and duocarmycin analogs via intramolecular aryl radical cyclization of a tethered vinyl chloride

The 5-exo-trig radical cyclization of an aryl halide onto a tethered vinyl chloride produces the 3-chloromethyl dihydroindole precursors for CC- 1065 and duocarmycin analogs with chlorine installed as a suitable leaving group for subsequent cyclopropane spirocyclization. The generality of this approach was examined in the context of six CC-1065 and duocarmycin analogs previously synthesized in this laboratory.