1044516-31-5Relevant articles and documents
Three-Component Coupling-Oxidative Amidation-Heterocycloannulation: Synthesis of the Indole Alkaloids Hamacanthin A and trans -2,5-Bis(3′-Indolyl)piperazine
Srinivasan, A. Kaliyaperumal,Banerjee, Shyamapada,Pachore, Sharad S.,Syam Kumar
, p. 1057 - 1064 (2017)
Concise and highly convergent syntheses of antifungal marine bis(indole) alkaloids, hamacanthin A and trans-2,5-bis(3′-indolyl)piperazine is described. The total synthesis of hamacanthin A is accomplished via the oxidative amidation-chemoselective heterocycloannulation of 2,2-dibromo-1-(1H-indol-3-yl)ethanone with 1-(1H-indol-3-yl)ethane-1,2-diamine. The reduction of desbromo hamacanthin with aluminum borohydride afforded the alkaloid trans-2,5-bis(3′-indolyl)piperazine. Two novel and convenient protocols for the synthesis of indolyl-1,2-diaminoethane are also developed in moderate to good yields.
1-(1H-indol-3-yl)ethanamine derivatives as potent Staphylococcus aureus NorA efflux pump inhibitors
Hequet, Arnaud,Burchak, Olga N.,Jeanty, Matthieu,Guinchard, Xavier,Le Pihive, Emmanuelle,Maigre, Laure,Bouhours, Pascale,Schneider, Dominique,Maurin, Max,Paris, Jean-Marc,Denis, Jean-Noel,Jolivalt, Claude
, p. 1534 - 1545 (2014/07/21)
The synthesis of 37 1-(1H-indol-3-yl)ethanamine derivatives, including 12 new compounds, was achieved through a series of simple and efficient chemical modifications. These indole derivatives displayed modest or no intrinsic anti-staphylococcal activity. By contrast, several of the compounds restored, in a concentration-dependent manner, the antibacterial activity of ciprofloxacin against Staphylococcus aureus strains that were resistant to fluoroquinolones due to overexpression of the NorA efflux pump. Structure-activity relationships studies revealed that the indolic aldonitrones halogenated at position 5 of the indole core were the most efficient inhibitors of the S. aureus NorA efflux pump. Among the compounds, (Z)-N-benzylidene-2-(tert-butoxycarbonylamino)-1-(5- iodo-1H-indol-3-yl)ethanamine oxide led to a fourfold decrease of the ciprofloxacin minimum inhibitory concentration against the SA-1199B strain when used at a concentration of 0.5 mg L-1. To the best of our knowledge, this activity is the highest reported to date for an indolic NorA inhibitor. In addition, a new antibacterial compound, tert-butyl (2-(3-hydroxyureido)-2-(1H- indol-3-yl)ethyl)carbamate, which is not toxic for human cells, was also found. A pump turn off: 1-(1H-Indol-3-yl)ethanamine derivatives such as the one shown here, were synthesized through simple chemical modifications and were shown to be efficient NorA efflux pump inhibitors. They are able to restore ciprofloxacin activity against fluoroquinolone-resistant Staphylococcus aureus strains.
NOVEL INDOLIC DERIVATIVES, THEIR PREPARATION PROCESSES AND THEIR USES IN PARTICULAR AS ANTIBACTERIALS
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Page/Page column 35-36, (2010/06/19)
The invention relates to the use of at least one compound of the formula (I), in which R and R3 are particularly a hydrogen atom, R1 is particularly a hydrogen atom or a methyl, ethyl or isobutyl mi group, R4, R5, R6 and R7 are independently a hydrogen atony, an alkoxyl group with 1 to 7 carbon atoms or a halogen atom, R2 is a hydrogen atom, an O? group or an OH group, B is an N-GP1 or NRc, group, GP1 being a Boc or Cbz group, and Rc is a hydrogen atom or a methyl or t-butyl group, for preparing a drug for treating conditions associated with bacterial infections, in particular for treating bacterial diseases.
