Day: November 18, 2022

Swaminathan, S. published the artcileSynthesis of ethyl 1-acetyl-2-(3-indolylmethyl)carbazate. An analog of Nα-acetyltryptophan ethyl ester, Recommanded Product: 2-Ethoxy-1H-indole, the main research area is .

Indole-3-carboxaldehyde (5 g.) in 100 ml. EtOH was added to a solution of 2.69 g. NH2NHAc in 10 ml. H2O containing 1 drop HOAc, and the mixture refluxed 2 hrs. to yield 4.5 g. 3-indolealdehyde acetohydrazone (I), m. 253-5° (EtOH). I (1 g.) in 150 ml. EtOH was hydrogenated 2.5 hrs. at 50 psi over Pd-BaCO3 to yield 0.75 g. 1-acetyl-2-(3-indolylmethyl)hydrazine (II), m. 147.5-8.5° (EtOAc-petr. ether). Et3N (1 g.) in 10 ml. C6H6 was added to a solution of 1 g. II in 100 ml. C6H6, followed by dropwise addition during 30 min. of a solution of 0.6 g. ClCO2Et in 29 ml. C6H6, and the mixture stirred 3 hrs., kept overnight, and worked up to yield 1.1 g. Et 1-acetyl-2-(3-indolylmethyl)carbazate (III), m. 91-2° (C6H6). III was of interest as a potential tryptophan antagonist. A mixture of 0.5 g. II in 20 ml. 40% alc. NaOH was refluxed 6 hrs., EtOH removed in vacuo, and the residue diluted with H2O to yield 0.275 g. 3-indolealdazine (IV), m.p. and mixed m.p. 310-12°. IV (0.5 g.) was also obtained by refluxing 1 g. I with 40 ml. 20% alc. NaOH. A mixture of 1.5 g. indole-3-aldehyde, 0.5 g. 98-100% N2H4.H2O, 10 ml. EtOH, and a drop HOAc was refluxed 1 hr. and cooled to yield 1.2 g. IV, m. 310-12° (Me2CO).

Indian Journal of Chemistry published new progress in CAplus about 1009-27-4, 1009-27-4 belongs to class indole-building-block, name is 2-Ethoxy-1H-indole, and the molecular formula is C10H11NO, Recommanded Product: 2-Ethoxy-1H-indole.

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Florvall, Lennart published the artcileSelective monoamine oxidase inhibitors. 3. Cyclic compounds related to 4-aminophenethylamine. Preparation and neuron-selective action of some 5-(2-aminoethyl)-2,3-dihydroindoles, Product Details of C8H8ClN, the main research area is monoamine oxidase inhibitor aminoethylindole; neuron selective aminoethylindole.

Nine (aminoethyl)dihydroindoles I (R = Me, Et; R1, R3 = H, Me; R2 = H, Cl, Me; R4 = H, Et) were prepared and tested as monoamine oxidase (MAO) inhibitors in vitro and in vivo. I are selective MAO-A inhibitors in vitro, the most active compounds, 5-[1-(2-aminopropyl)]-2,3-dihydro-4-methylindole acetate (II), 5-[1-(2-aminopropyl)]-4-chloro-2,3-dihydroindole acetate, 5-[1-(2-aminopropyl)]-2,3-dihydro-1-ethyl-4-methylindole tartrate (III), 5-[1-(2-aminopropyl)]-2,3-dihydro-1-ethyl-6-methylindole tartrate, and 5-[1-(2-aminobutyl)]-4-chloro-2,3-dihydroindole acetate being equipotent with amiflamine. II, III, 5-[1-(2-aminopropyl)]-2,3-dihydroindole acetate (IV), and 5-[1-(2-amino-2-methylpropyl)]-2,3-dihydroindole acetate were very potent inhibitors of MAO in serotonergic and/or noradrenergic nerve terminals in the rat brain in vivo, inhibiting MAO within these neurons at doses 1/10 of those required to inhibit MAO in other neurons or cells. IV was also a potent and selective inhibitor of MAO within dopaminergic nerve terminals in vivo.

Journal of Medicinal Chemistry published new progress about monoamine oxidase inhibitor aminoethylindole; neuron selective aminoethylindole. 41910-64-9 belongs to class indole-building-block, name is 4-Chloroindoline, and the molecular formula is C8H8ClN, Product Details of C8H8ClN.

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Lavrenov, Sergei N. published the artcileSynthesis of methyl 5- and 6-nitroindole-2-carboxylates by nitration of indoline-2-carboxylic acid, COA of Formula: C10H8N2O4, the main research area is methyl nitro indole carboxylate nitration; indoline carboxylic acid methyl ester nitro preparation.

Indoline-2-carboxylic acid was transformed into 6-nitroindoline-2-carboxylic acid, the Me ester of which was easily dehydrogenated by DDQ to Me 6-nitroindole-2-carboxylate (total yield: 67%). Me 5-nitroindole-2-carboxylate was obtained by the nitration of Me 1-acetylindoline-2-carboxylate acid followed by dehydrogenation with MnO2 in toluene in 40% total yield.

Synthesis published new progress about methyl nitro indole carboxylate nitration; indoline carboxylic acid methyl ester nitro preparation. 136818-66-1 belongs to class indole-building-block, name is Methyl 6-nitro-1H-indole-2-carboxylate, and the molecular formula is C10H8N2O4, COA of Formula: C10H8N2O4.

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Benghiat, Eric published the artcileSynthesis of S-3-indolemethyl derivatives of 5′-deoxy-5′-thioadenosine, Synthetic Route of 5654-92-2, the main research area is indolylmethylthiodeoxyadenosine; adenosine indolylmethylthiodeoxy.

The title compounds (I; R = H, Me) were prepared by reaction of the appropriate 3-indolemethyl thioacetate with 5′-deoxy-5′-chloroadenosine in basic media. 5′-Deoxy-5′-(3-indolemethylthio)adenosines unsubstituted at the indolic nitrogen, cannot be prepared via this route due to facile conversion of the precursor 3-indolemethylthiol derivative to the corresponding 3,3′-diindolemethyl sulfide.

Journal of Heterocyclic Chemistry published new progress about indolylmethylthiodeoxyadenosine; adenosine indolylmethylthiodeoxy. 5654-92-2 belongs to class indole-building-block, name is N,N-Dimethyl-1-(1H-pyrrolo[2,3-b]pyridin-3-yl)methanamine, and the molecular formula is C10H13N3, Synthetic Route of 5654-92-2.

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Eskola, Olli published the artcileSynthesis of 3-[[4-(4-[18F]fluorophenyl)piperazin-1-yl]methyl]-1H-pyrrolo[2,3-b]pyridine, Quality Control of 5654-92-2, the main research area is fluorophenylpiperazinylmethylpyrrolopyridine preparation biodistribution.

3-[[4-(4-[18F]fluorophenyl)piperazin-1-yl]methyl]-1H-pyrrolo[2,3-b]pyridine, a candidate to image dopamine D4 receptors, was synthesized via electrophilic fluorination of a trimethylstannyl precursor with high specific radioactivity [18F]F2. The precursor was obtained by a facile four-step synthetic approach; the trimethylstannyl leaving group was introduced by displacement of iodine utilizing palladium catalysis and hexamethyldistannane in an inert solvent. The total radiosynthesis time was 50 min, including purification and formulation for injection. Decay corrected radiochem. yield was <1% as calculated from the amount of [18F]F- produced. Specific radioactivity at the end of synthesis was 12.8-16.4 GBq/μmol. Radiochem. purity was 88-92%. Ex vivo studies in rats showed homogeneous distribution of radioactivity within rat brain. Journal of Labelled Compounds & Radiopharmaceuticals published new progress about fluorophenylpiperazinylmethylpyrrolopyridine preparation biodistribution. 5654-92-2 belongs to class indole-building-block, name is N,N-Dimethyl-1-(1H-pyrrolo[2,3-b]pyridin-3-yl)methanamine, and the molecular formula is C10H13N3, Quality Control of 5654-92-2.

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Hlavac, Jan published the artcileSynthesis of oxo analogs of Lamotrigine and related compounds, Safety of 4,5-Dichloroisatin, the main research area is azauracil preparation coupling cyanoacetylcarbamate; Lamotrigine oxo analog preparation; triazinedione functionalized preparation; indolotriazinone preparation.

Lamotrigine oxo analogs I (R1 = H, Cl, Br, iodo, HO) were prepared from azauracil I (R1 = NH2) via the formation of the intermediate diazonium salt. Coupling of this diazonium salt with Et cyanoacetylcarbamate gave the corresponding carbamoyl hydrazone, which underwent intramol. cyclization upon reflux in pyridine to afford bis(triazinyl)benzene II containing two 6-azauracil rings.

ARKIVOC (Gainesville, FL, United States) published new progress about azauracil preparation coupling cyanoacetylcarbamate; Lamotrigine oxo analog preparation; triazinedione functionalized preparation; indolotriazinone preparation. 1677-47-0 belongs to class indole-building-block, name is 4,5-Dichloroisatin, and the molecular formula is C8H3Cl2NO2, Safety of 4,5-Dichloroisatin.

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Sanchez-Obregon, Ruben published the artcileSynthesis of a potential fluorescence probe, (-)-(R)-7-azatryptophan, via alkylation of the (1R,4R)-camphor imine of tert-butylglycinate, COA of Formula: C10H13N3, the main research area is azatryptophan; bornylidenaminoacetate alkylation iodomethylazaindole.

The synthesis of (-)-(R)-7-azatryptophan (I) from com. available 7-azaindole is described. The key step involved the diastereoselective alkylation of the bornylideneaminoacetate II with 1-(tert-butoxycarbonyl-3-(iodomethyl)-7-azaindole. The alkylation, conducted at -100° in THF/HMPA using KN(SiMe3)2 as the base, afforded imine III in >98% diastereomeric excess. Hydrolysis and deprotection of III gave I.

Canadian Journal of Chemistry published new progress about azatryptophan; bornylidenaminoacetate alkylation iodomethylazaindole. 5654-92-2 belongs to class indole-building-block, name is N,N-Dimethyl-1-(1H-pyrrolo[2,3-b]pyridin-3-yl)methanamine, and the molecular formula is C10H13N3, COA of Formula: C10H13N3.

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Bremer, Paul T. published the artcileNewly Designed Quinolinol Inhibitors Mitigate the Effects of Botulinum Neurotoxin A in Enzymatic, Cell-Based, and ex Vivo Assays, HPLC of Formula: 41910-64-9, the main research area is quinolinol sulfonamide preparation botulinum neurotoxin inhibitor botulism.

Botulinum neurotoxin A (BoNT/A) is one of the most deadly toxins, and is the etiol. agent of the potentially fatal condition, botulism. Herein, the authors investigated 8-hydroxyquinoline (quinolin-8-ol) as a potential inhibitor scaffold for preventing the deadly neurochem. effects of the toxin. Quinolinols are known chelators that can disrupt the BoNT/A metalloprotease zinc-containing active site, thus impeding its proteolysis of the endogenous protein substrate, synaptosomal-associated protein 25 (SNAP-25). Using this information, the structure-activity relationship (SAR) of the quinolinol-5-sulfonamide scaffold was explored through preparation of a crude sulfonamide library, and evaluating the library in a BoNT/A LC enzymic assay. Potency optimization of the sulfonamide hit compounds was undertaken as informed by docking studies, granting a lead compound with a submicromolar Ki. These quinolinol analogs demonstrated inhibitory activity in a cell-based model for SNAP-25 cleavage and an ex vivo assay for BoNT/A-mediated muscle paralysis.

Journal of Medicinal Chemistry published new progress about Botulism. 41910-64-9 belongs to class indole-building-block, name is 4-Chloroindoline, and the molecular formula is C8H8ClN, HPLC of Formula: 41910-64-9.

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Gao, Mingzhang published the artcileSynthesis of carbon-11-labeled 4-aryl-4H-chromenes as new PET agents for imaging of apoptosis in cancer, Name: 4-(Benzyloxy)-1-methyl-1H-indole, the main research area is arylbenzopyrancarbonitrile carbon 11 preparation PET imaging apoptosis.

Carbon-11-labeled 4-aryl-4H-chromenes, 4-(3-[11C]methoxy-5-methoxyphenyl)-, 4-(3-bromo-4-[11C]methoxy-5-methoxyphenyl)-, 4-(3-[11C]methoxy-5-methoxyphenyl)-, 4-(3-bromo-4-[11C]methoxy-5-methoxyphenyl)-, 4-(3-[11C]methoxy-5-methoxyphenyl)-, 4-(3-bromo-4-[11C]methoxy-5-methoxyphenyl)-, 4-(3-[11C]methoxy-5-methoxyphenyl)- and 4-(3-bromo-4-[11C]methoxy-5-methoxyphenyl)–2-amino-7-methyl-4,7-dihydropyrano[2,3-e]indole-3-carbonitrile were prepared by O-[11C]methylation of their alc. precursors using [11C]CH3OTf under basic conditions and isolated by a simplified solid-phase extraction (SPE) method in 30-50% radiochem. yields based on [11C]CO2 and decay corrected to end of bombardment (EOB). The overall synthesis time from EOB was 15-20 min, the radiochem. purity was >99%, and the specific activity at end of synthesis (EOS) was 111-185 GBq/μmol.

Applied Radiation and Isotopes published new progress about Apoptosis. 13523-93-8 belongs to class indole-building-block, name is 4-(Benzyloxy)-1-methyl-1H-indole, and the molecular formula is C16H15NO, Name: 4-(Benzyloxy)-1-methyl-1H-indole.

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Baader, Manuel published the artcileCharacterization of the properties of a selective, orally bioavailable autotaxin inhibitor in preclinical models of advanced stages of liver fibrosis, Recommanded Product: N,N-Dimethyl-1-(1H-pyrrolo[2,3-b]pyridin-3-yl)methanamine, the main research area is autotaxin inhibitor bioavailability pharmacokinetics hepatitis liver fibrosis.

Autotaxin (ATX) is a secreted phospholipase which hydrolyzes lysophosphatidylcholine to generate lysophosphatidic acid (LPA). The extracellular signalling mol. LPA exerts its biol. actions through activation of six GPCRs expressed in various cell types including fibroblasts. Multiple preclin. studies using knockout animals, LPA receptor antagonists or ATX inhibitors have provided evidence for a potential role of the ATX/LPA axis in tissue fibrosis. Despite growing evidence for a correlation between ATX levels and the degree of fibrosis in chronic liver diseases, including viral hepatitis and hepatocellular carcinoma, the role of ATX in non-alc. steatohepatitis (NASH) remains unclear. The relevance of ATX in the pathogenesis of liver fibrosis was investigated by oral administration of Ex_31, a selective ATX inhibitor, in a 10 wk model of carbon tetrachloride-induced liver injury and in a 14 wk model of choline-deficient amino acid-defined diet-induced liver injury in rats. Oral administration of Ex_31, a selective ATX inhibitor, at 15 mg·kg-1 twice daily in therapeutic intervention mode resulted in efficient ATX inhibition and more than 95% reduction in plasma LPA levels in both studies. Treatment with Ex_31 had no effect on biomarkers of liver function, inflammation, or fibrosis and did not result in histol. improvements in diseased animals. Our findings question the role of ATX in the pathogenesis of hepatic fibrosis and the potential of small mol. ATX inhibitors for the treatment of patients with NASH and advanced stages of liver fibrosis.

British Journal of Pharmacology published new progress about Apoptosis. 5654-92-2 belongs to class indole-building-block, name is N,N-Dimethyl-1-(1H-pyrrolo[2,3-b]pyridin-3-yl)methanamine, and the molecular formula is C10H13N3, Recommanded Product: N,N-Dimethyl-1-(1H-pyrrolo[2,3-b]pyridin-3-yl)methanamine.

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles