- Development of large-scale preparations of indole derivatives: Evaluation of potential thermal hazards and studies of reaction kinetics and mechanisms
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Hydrogenation of (E)-2-nitropyrrolidinostyrene in the presence of the doped rhodium catalyst is safe, scalable, and highly effective for the preparation of 6-benzyloxyindole. Reaction kinetics with/without additives also were examined using in situ IR for
- Akao, Atsushi,Nonoyama, Nobuaki,Mase, Toshiaki,Yasuda, Nobuyoshi
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p. 1178 - 1183
(2012/12/23)
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- Highly chemoselective reduction using a Rh/C-Fe(OAc)2 system: Practical synthesis of functionalized indoles
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Here, we report a highly effective and chemoselective method of preparing substituted indoles from (E)-2-nitropyrrolidinostyrenes via hydrogenation in the presence of a rhodium catalyst doped by additives such as Ni(NO 3)2·6H2O, Fe(OAc)2 or Co(acac)3. These hydrogenation conditions may also be applied to other substrates. Aromatic nitro compounds and olefins can be selectively reduced in the presence of aromatic benzyl ethers, aromatic halides and aromatic aldehydes.
- Akao, Atsushi,Sato, Kimihiko,Nonoyama, Nobuaki,Mase, Toshiaki,Yasuda, Nobuyoshi
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p. 969 - 972
(2007/10/03)
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- PROCESS FOR PRODUCING INDOLOPYRROLOCARBAZOLE DERIVATIVE
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The present invention provides a process for industrially advantageously producing a compound represented by the formula (I): or a pharmaceutically acceptable salt thereof, which is useful as an anticancer agent, and also provides a catalyst used for hydrogenation reaction in the process.
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Page/Page column 39-40
(2010/02/11)
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- 1,3,6-Trisubstituted indoles as peptidoleukotriene antagonists: Benefits of a second, polar, pyrrole substituent
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1,6-Substituted and 3,5-substituted indoles and indazoles containing acylamino and N-arylsulfonyl amide appendages are potent antagonists of the peptidoleukotrienes LTD4 and LTE4. A compound from the 3,5-substituted indole series, N-[4-[[5-[[(cyclopentyloxy)carbonyl]amino]-1-methylindol-3- yl]methyl]-3-methoxybenzoyl]-2-methyl-benzenesulfonamide (ICI 204,219), is undergoing clinical evaluation for asthma. Two new elements of structural diversity were introduced to this series of antagonists. An investigation of pyrrole substituents in the 1,6-substituted indoles demonstrated that substitution at C-2 was detrimental to biological activity, but the incorporation of hydrophilic groups at C-3 was beneficial. The introduction of a propionamide moiety at C-3 enhanced activity by 1 order of magnitude; N- [4-[[6-(cyclopentylacetamido)-3-[2-(N-methylcarbamoyl)ethyl]indol-1- yl]methyl]-3-methoxybenzoyl]benzenesulfonamide (15c) has a pK(B) of 10.7 at the LTD4 receptor on guinea pig trachea. Modifications of the acylamino portion of the disubstituted antagonists demonstrated that a transposition of the amide CO and NH atoms was viable. N-Cyclopentylmethyl amides in both the 1,6- and 3,5-disubstituted indole series were 1 order of magnitude less potent than the corresponding cyclopentylacetamides. In both series this potency loss could be regained by the incorporation of a propionamide substituent at either C-3 or N-1, respectively. For example, N-[4-[[6-[N- (cyclopentylmethyl)carbamoyl]-3-[2-(pyrrolidin-1-ylcarbonyl)ethyl]indol-1- yl]methyl]-3-methoxybenzoyl]-2-methylbenzenesulfonamide (39c) has a pK(B) of 9.5.
- Brown,Cronk,Aharony,Snyder
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p. 2419 - 2439
(2007/10/02)
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- HYDROXYLATION OF INDOLINES AND INDOLES BY HYDROGEN PEROXIDE IN SUPERACIDS
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In SbF5-HF, indolines and indoles are hydroxylated on the aromatic ring, protonated hydrogen peroxide H3O2+ reacting on the protonated substrates.
- Berrier, Christian,Jacquesy, Jean-Claude,Jouannetaud, Marie-Paule,Renoux, Alain
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p. 4565 - 4568
(2007/10/02)
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