7633-56-9

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 88, p. 4061, 1966 DOI: 10.1021/ja00969a030

Upstream product

• 7633-57-0 1-nitrosoindoline 
• 496-15-1 1-indoline 

Downstream Products

• 33244-59-6 2-methyl-3-phenyl-4,5-dihydro-pyrrolo[3,2,1-hi]indole 
• 92199-07-0 7-phenylindoline 
• 104636-54-6 5-phenyl-2,3-dihydroindole 
• 31401-55-5 7,8-dimethyl-4,5-dihydropyrrolo<3.2.1-hi>indole 
• 344904-65-0 (Z)-6-[4-(2,3-Dihydro-indol-1-ylcarbamoyl)-phenyl]-hex-5-enoic acid 
• 271-29-4 6-azaindole 
• 1226977-16-7 N-[2-(phenylethynyl)benzylidene]indolin-1-amine 

Relevant academic research and scientific papers

Diaza [1,4] Wittig-type rearrangement of N-allylic-N-Boc-hydrazines into γ-amino- N -Boc-enamines

Diaza [1,4] Wittig-type rearrangement of N-allylic-N-Boc-hydrazines into γ-amino-N-Boc-enamines was demonstrated. The scope and limitation, experimental mechanistic studies, and a proposed reaction mechanism were also described.

1-[(imidazolin-2-yl)amino]indoline and 1-[(imidazolin-2-yl)amino]1,2,3,4-tetrahydroquinoline derivatives: New insights into their circulatory activities

N-[(Imidazolin-2-yl)amino]indolines and N-[(imidazolin-2-yl)amino]-1,2,3,4-tetrahydroquinolines, previously described in patent literature as hypertensive agents, were synthesized and tested in vitro for their affinities to α1- and α2-adrenoceptors as well as imidazoline I1 and I2 receptors. The compounds most potent at either α1- or α2-adrenoceptors were administered intravenously to normotensive Wistar rats to determine their effects on mean arterial blood pressure and heart rate. Upon intravenous administration at dose of 0.1 mg/kg to normotensive male Wistar rats, the initial transient pressor effect was followed by long-lasting hypotension and bradycardia. In view of the above results the 1-[(imidazolin-2-yl)amino]indolines and [(imidazolin-2-yl)amino]-1,2,3,4-tetrahydroquinolines are now found to possess circulatory profile characteristic of the centrally acting clonidine-like hypotensive imidazolines.

3-(Hetero)aryl-4-indolylamino-α-tetralones by diastereoselective internal redox cyclization: An "azaenamine" conjugate addition

(E)-3-(Hetero)aryl-1-(2-((E)-(indolin-1-ylimino)methyl)phenyl) prop-2-en-1-ones 1 undergo 6-exo-trig cyclization reactions upon treatment with BF3?Me2S in dichloromethane at low temperature to give the tetralones 10 in good yield. Th

1H-Indole-Pyridinecarboxamide and 1H-Indole-Piperidinecarboxamide Compounds

Compounds of formula (I): wherein: A represents a divalent radical: wherein: Z represents an oxygen atom or a sulphur atom,R6 represents a hydrogen atom, an alkyl, alkenyl, arylalkyl or polyhaloalkyl group or a substituted, linear or branched alkyl chain, represents a single bond or a double bond,R1, R2, R3 and R4 represent a hydrogen or halogen atom,an alkyl, alkoxy, hydroxy, cyano, nitro, polyhaloalkyl or optionally substituted amino group, or a linear or branched alkyl chain substituted by one or more groups,R5 represents a hydrogen atom or an alkyl, aminoalkyl or hydroxyalkyl group,X and Y represent a hydrogen atom or an alkyl group,Ra, Rb, Rc and Rd represent a hydrogen or halogen atom, an alkyl, hydroxy, alkoxy, cyano, nitro, polyhaloalkyl, optionally substituted amino group, or a substituted, linear or branched alkyl chain,Re represents a hydrogen atom or an alkyl, arylalkyl or alkenyl group or a substituted, linear or branched alkyl chain, their enantiomers, diastereoisomers, and N-oxides, and also addition salts thereof with a pharmaceutically acceptable acid or base.

TETRACYCLIC INDOLES AS POTASSIUM CHANNEL MODULATORS

The present invention is directed to compounds of Formula I: that are potassium channel modulators and pharmaceutical compositions thereof. The present invention is further directed to methods of treatment using the compounds and pharmaceutical compositions of the invention. The present invention is still further directed to synthetic processes for producing the compounds of the invention.

COMPOSITIONS AND METHODS FOR TREATMENT OF CANCER

The present invention relates to pyrrolidine-2,5-dione compounds, and methods of preparation of these compounds. The present invention also relates to pharmaceutical compositions comprising pyrrolidine-2,5-dione compounds. The present invention provides methods of treating a cell proliferative disorder, such as a cancer, by administering to a subject in need thereof a therapeutically effective amount of a compound or pyrrolidine-2,5-dione compound of the present invention.

Structure - Antitussive activity relationships of naltrindole derivatives. Identification of novel and potent antitussive agents

We have previously reported antitussive effects of naltrindole (NTI), a typical δ opioid receptor antagonist, in a rat model. The ED50 values of NTI by intraperitoneal and peroral injections were 104 μg/kg and 1840 μg/kg, respectively, comparable to those of codeine. Codeine, one of the most reliable centrally acting antitussive drugs, has μ agonist activity and thus the same side effects as morphine, e.g., constipation, dependency, and respiratory depression. Because NTI is a δ opioid antagonist, its derivatives have potential as highly potent antitussives, free from the μ opioid agonist side effects. We attempted to optimize the NTI derivatives to develop novel antitussive agents. On the basis of the studies of structure - antitussive activity relationships of alkyl substituted NTI derivatives, we designed NTI derivatives with extra ring fused structures. As a clinical candidate, we identified a highly potent new compound, (5R,9R,13S,14S)-17- cyclopropylmethyl-6,7-didehydro-4,5-epoxy-5′,6′-dihydro-3-methoxy- 4′H-pyrrolo[3,2,1-ij]quinolino[2′,1′:6,7]morphinan-14-ol (5b) methanesulfonate (TRK-850) which was effective even by oral administration (ED50 6.40 μg/kg).

N-aminoindoline derivatives as inhibitors of 5-lipoxygenase

N-Aminoindoline derivatives were prepared and their 5-lipoxygenase inhibitory activities were evaluated in vitro and compared with those of phenidone and NDGA. Compound 4 presents the most effective 5-LO inhibition.

3-substituted cephem compounds

The present invention relates to novel cephalosporins of the formula (I); STR1 wherein, R1 represents a C1 ?C4 alkyl group or STR2 wherein, R2 and R3, independently, represent hydrogen or a C1 ?C3 alkyl group and R4 represents hydrogen or a C1 ?C4 alkyl group; R1a represents hydrogen or an amino-protecting group; Q represents CH or N; and the formula STR3 represents a saturated or unsaturated heterocyclic group which contains 1 to 4 nitrogen atoms of which one is substituted with an amino group to form quaternary ammonium, and oxygen or sulfur, or a fused heterocyclic group thereof formed together with a substituted or unsubstituted benzene or an optional heterocyclic group, or a pharmaceutically acceptable salt thereof, to processes for preparing the same and to a pharmaceutical composition containing the same as an active ingredient. The compounds(1) according to the invention exhibit potent antibacterial activity and broad antibacterial spectrum against the Gram-positive strains including Staphylococcus as well as Gram-negative strains including Pseudomonas, and, therefore, are expected to be very useful in treatment of various diseases caused by bacterial infection in human beings and animals.

Development of high-affinity 5-HT3 receptor antagonists. Structure- affinity relationships of novel 1,7-annelated indole derivatives. 1

On the basis of the structures of ondansetron and GR 65,630, its ring- opened C-linked methylimidazole analogue, novel 1,7-annelated indole derivatives were synthesized as potential 5-HT3 antagonists. Receptor binding studies show that all compounds display a high affinity for the 5- HT3 receptors. In both series annelation results in compounds being 7 and 4 times more potent than the references ondansetron and GR 65,630, respectively. Similar to ondansetron, the 1,7-annelated indoles show little stereoselectivity. The (-)-isomers are only slightly more potent than the (+)-isomers. The receptor binding profile of l-10-[(2-methyl-1H-imidazol-1- yl)methyl]-5,6,8,9,10,11-hexahydro-4H-pyrido[3,2,1-jk]carbazol-11-one hydrochloride (24b) (INN cilansetron) shows that the compound displays, besides a high affinity for 5-HT3 receptors (K(i) = 0.19 nM), a weak affinity for σ-receptors (K(i) = 340 nM), muscarine M1 receptors (K(i) = 910 nM), and 5-HT4 receptors (K(i) = 960 nM) and no affinity (K(i) ≥ 5000 nM) for all the other receptor types tested (n = 37). The new compounds fit the proposed necessary chemical template for binding: a heteroaromatic ring system, a coplanar carbonyl group, and a nitrogen center at well-defined distances. The enhanced potency of the annelated 1,7-indole derivatives indicates that the extra ring provides a favorable hydrophobic area for interaction with the 5-HT3 receptor site. In vivo cilansetron is more potent and induces less central side effects than ondansetron. At present cilansetron is in clinical trials.