Day: October 26, 2022

Bandini, Marco; Gualandi, Andrea; Monari, Magda; Romaniello, Alessandro; Savoia, Diego; Tragni, Michele published an article in 2010, the title of the article was Allylic alcohols: Valuable synthetic equivalents of non-activated alkenes in gold-catalyzed enantioselective alkylation of indoles.SDS of cas: 883526-76-9 And the article contains the following content:

The recent booming of gold catalysis has demonstrated that unprecedented transformations can be realized in a highly selective manner. Moreover, due to the growing availability of chiral organic ligands, gold-catalysis can be considered as one of most dynamic hot spots in asym. synthesis. However, in this context, the use of non-activated olefinic C-C double bonds is still largely unexplored due to the intrinsic inertness of C=C (respect to allenes and alkynes) in taking part in nucleophilic additions assisted by π-electrophilic activations. Allylic alcs. have been demonstrated to be feasible “surrogates” of non-activated alkenes for the enantioselective allylic alkylation of indoles catalyzed by chiral gold(I) complexes. In this investigation, a full account addressing efficiency and substrate scope of such a process is presented. The products, tetrahydrocarbazoles or tetrahydro-β-carbolines, are obtained in moderate to good yields and 40-86% ee from the corresponding Z-allylic alc.-containing substrates, while the E isomers are unreactive. The experimental process involved the reaction of 1,5-Dimethyl-1H-indole-2-carbaldehyde(cas: 883526-76-9).SDS of cas: 883526-76-9

The Article related to allylic alc tethered indole derivative preparation, chiral ligand gold catalyzed intramol allylic alkylation indole derivative, tetrahydrocarbazole derivative stereoselective preparation, tetrahydrocarboline derivative stereoselective preparation and other aspects.SDS of cas: 883526-76-9

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

On December 19, 1996, Arnold, Lee D.; Moyer, Mikel P.; Sobolov-jaynes, Susan B. published a patent.COA of Formula: C8H8ClN The title of the patent was Preparation of heterocyclic ring-fused pyrimidines for treatment of hyperproliferative diseases. And the patent contained the following:

The title compounds [I; Y = (un)substituted unsaturated or aromatic 5- or 6-membered ring (together with the carbons to which it is attached) containing one to three heteroatoms such as S, O, N (at least one of said heteroatoms is N); Z = NR1R2 (wherein R1 = H; R2 = (un)substituted Ph, heterocycle)], useful in the treatment of hyperproliferative diseases, such as cancers, and psoriasis or benign prostatic hyperplasia, were prepared Thus, reaction of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine with 3-aminophenylacetylene in pyridine afforded 12% II.HCl. In general, compounds I were effective at 0.2-2.5 g/day for an average 70 kg human. The experimental process involved the reaction of 6-Chloro-2,3-dihydro-1H-indole(cas: 52537-00-5).COA of Formula: C8H8ClN

The Article related to pyrimidine heterocyclyl fused preparation hyperproliferative disease, antitumor agent heterocyclopyrimidine fused preparation, psoriasis heterocyclopyrimidine fused preparation, benign prostatic hyperplasia heterocyclopyrimidine fused preparation and other aspects.COA of Formula: 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

On May 26, 2020, Jia, Wei-Guo; Gao, Li-Li; Wang, Zhi-Bao; Wang, Jing-Jing; Sheng, En-Hong; Han, Ying-Feng published an article.Formula: C8H8ClN The title of the article was NHC-Palladium(II) Mononuclear and Binuclear Complexes Containing Phenylene-Bridged Bis(thione) Ligands: Synthesis, Characterization, and Catalytic Activities. And the article contained the following:

Mono- and binuclear Pd(II) complexes with N-heterocyclic carbene (NHC) and phenylene-bridged bis(thione) (SCS) ligands were prepared and characterized by 1H and 13C NMR spectroscopy, IR, and mass spectrometry. The mol. structures of 1b, 2a, and 3b were determined by the single-crystal x-ray diffraction method. The catalytic activities of the synthesized Pd complexes in the regioselective reduction of quinolines to the corresponding 1,2,3,4-tetrahydroquinolines were thoroughly studied with NH3-borane under mild reaction conditions. The activities of the binuclear Pd(NHC) complexes were higher than those of the corresponding mononuclear complexes under the same conditions. The experimental process involved the reaction of 6-Chloro-2,3-dihydro-1H-indole(cas: 52537-00-5).Formula: C8H8ClN

The Article related to imidazolylidene palladium phenylene bridged dithione complex preparation reduction catalyst, crystal structure imidazolylidene palladium phenylene bridged dithione complex, mol structure imidazolylidene palladium phenylene bridged dithione complex and other aspects.Formula: 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

On April 20, 2017, Lin, Wenbin; Manna, Kuntal; Ji, Pengfei published a patent.Category: indole-building-block The title of the patent was Stabilization of active metal catalysts at metal-organic framework nodes for highly efficient organic transformations. And the patent contained the following:

Metal-organic framework (MOFs) compositions based on post not synthetic metalation of secondary building unit (SBU) terminal or bridging OH or OH2 groups with metal precursors or other post-synthetic manipulations are described. The MOFs provide a versatile family of recyclable and reusable single-site solid catalysts for catalyzing a variety of asym. organic transformations, including the regioselective borylation and silylation of benzyiic C-H bonds, the hydrogenation of aikenes, imines, carbonyls, nitroarenes, and heterocycles, hydroboration, hydrophosphination, and cyclization reactions. The solid catalysts can also be integrated into a flow reactor or a supercritical fluid reactor. The experimental process involved the reaction of 6-Chloro-2,3-dihydro-1H-indole(cas: 52537-00-5).Category: indole-building-block

The Article related to zirconium cobalt benzenebisphenylcarboxylato terphenyldicarboxylato methanetetrakisbiphenylcarboxylato trimesato biphenyldicarboxyiato complex preparation, catalyst zirconium cobalt benzenebisphenylcarboxylato trimesato biphenyldicarboxyiato complex and other aspects.Category: indole-building-block

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

On September 29, 2011, Tajima, Nobumitsu; Yamashita, Atsuyuki; Kondo, Yurie; Chikamatsu, Kaori; Hiramatsu, Naoki; Makino, Mitsuhiro; Kitamoto, Katsunori; Kataoka, Daisuke; Nagai, Kazushige; Goto, Izumi; Torii, Masashi; Suzuki, Kimie; Iwai, Hisakazu; Hirooka, Hiroko published a patent.Safety of Methyl 2-(6-bromo-1H-indol-3-yl)acetate The title of the patent was Preparation of novel indole derivatives ad glucokinase activators. And the patent contained the following:

The providing of compound which has a glucokinase activating action. N-heterocyclyl-2-indolylproppanamide derivatives [I; a solid line with a —- line = a single bond or a double bond; X-C-Y with a —- line = N-C:C or C:C-N; R1 = H, C1-6 alkyl, C2-6 alkenyl, C1-6 alkylsulfonyl, C1-6 alkyl-arylsulfonyl, arylsulfonyl, alkanoyl, aroyl, C1-6 alkylsulfonyl-aralkyl, aralkyl, alkanoylaryl, aryl, carboxyl-C1-6 alkyl, halo-C1-6 alkyl, hydroxy-C1-6 alkyl, amino-C1-6 alkyl, carbamoyl-C1-6 alkyl, etc.; R2 = H, C1-6 alkyl; R3 = C1-6 alkyl, C3-7 cycloalkyl, heteroaryl; R4 = H, halo, NO2; R5 = H, C1-6 alkyl, halo, aryl, C1-6 alkoxy, aralkyloxy, aroyl, alkanoyl; R6 = H, halo, alkanoyl-aryl, aryl, HO, aralkyloxy, C1-6 alkoxy, alkanoyl-C1-6 alkoxy, aroyl-C1-6 alkoxy, alkanoylaryloxy, aryloxy, NO2, alkanoyl, (un)substituted aroyl, CO2H, C1-6 alkoxycarbonyl, heteroaryl, aryl-C1-6 alkyl, aryl-hydroxy-C1-6 alkyl, etc.; R7 = H, C1-6 alkyl, halo, alkanoyl; R1 and R7 together with X-C-C to which they are attached form cyclohexanone ring; A ring = 5- or 6-membered monocyclic N-containing heterocyclyl optionally containing addnl. N or S which optionally fused to aryl or C5-7 cycloalkyl to form bicyclic heterocyclic ring, in particular thiazolyl, pyridyl, or benzothiazolyl; R8 = H, halo, NO2, cyano, C1-6 alkoxycarbonyl, aralkyloxycarbonyl, HO, CO2H, (un)substituted CONH2, carboxy-C1-6 alkyl, etc. ] or prodrugs thereof or pharmaceutically acceptable salts thereof. These compounds have glucokinase activating activity and are useful for the prevention or treatment of diabetes or diabetes complications such as diabetic retinopathy, diabetic nephropathy, diabetic neuropathy, ischemic heart diseases, or arteriosclerosis. Thus, 9.4 mg 2-(6-acetyl-5-fluoro-1-methyl-1H-indol-3-yl)-3-cyclopentylpropionic acid was dissolved in 1.5 mL DMF , treated with 86.3 mg 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride and 48.6 mg 1-hydroxy-1H-benzotriazole monohydrate, stirred at room temperature for 2 h, treated with 178 mg 1-[2-(2-Aminothiazol-4-yl)acetyl]piperidine-4-carboxylic acid Et ester, stirred at 70° for 20 h to give, after workup and thin layer silica gel chromatog., 93% 1-[2-[2-[[2-(6-acetyl-5-fluoro-1-methyl-1H-indol-3-yl)-3-cyclopentylpropionyl]amino]thiazol-4-yl]acetyl]piperidine-4-carboxylic acid Et ester (II). II and compound (III) activated human glucokinase by 539 and 1,048 fold, resp., in in vitro phosphorylation of D-glucose with ATP. The experimental process involved the reaction of Methyl 2-(6-bromo-1H-indol-3-yl)acetate(cas: 152213-63-3).Safety of Methyl 2-(6-bromo-1H-indol-3-yl)acetate

The Article related to indole preparation prevention treatment diabetes, diabetes complication prevention treatment indole preparation, heterocyclylindolylproppanamide preparation glucokinase activator, pyridylindolylcyclopentylpropanamide preparation glucokinase activator and other aspects.Safety of Methyl 2-(6-bromo-1H-indol-3-yl)acetate

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

On November 30, 2022, Riegel, George F.; Payne, Curtis; Kass, Steven R. published an article.Safety of H-Idc-OH The title of the article was Effects of Broensted acid cocatalysts on the activities and selectivities of charge-enhanced thiourea organocatalysts in Friedel-Crafts and oxa-Pictet-Spengler reactions. And the article contained the following:

Charge-enhanced chiral thioureas were used in the organocatalysis of the Friedel-Crafts alkylation of indole with trans-β-nitrostyrene and the oxa-Pictet-Spengler reaction of tryptophol and benzaldehyde. The effects of substoichiometric Broensted acidic additives on the reaction conversions and enantiomeric ratios of these transformations were examined and the role of these species in the mechanism of the latter reaction was explored using variable time normalization kinetics to elucidate the reaction order of the catalyst, cocatalyst and reagents. A proposed pathway for the oxa-Pictet-Spengler cyclization that involves matched and mismatched catalyst and cocatalyst pairs and an off-cycle racemization of the latter species was provided. The experimental process involved the reaction of H-Idc-OH(cas: 79815-20-6).Safety of H-Idc-OH

The Article related to nitrostyrene indole thiourea organocatalyst enantioselective friedel crafts alkylation, nitro phenyl ethyl indole preparation, benzaldehyde tryptophol thiourea organocatalyst enantioselective oxa pictet spengler reaction, phenyl pyranoindole preparation and other aspects.Safety of H-Idc-OH

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

Hayashi, Shigeo; Ohashi, Katsuyo; Nakata, Eriko; Emoto, Chie published an article in 2012, the title of the article was Discovery of 1-(β-amino substituted-β-alanyl)-N,N-dimethylindoline-2-carboxamides as novel nonpeptide antagonists of nociceptin/orphanin FQ receptor: Efficient design, synthesis, and structure-activity relationship studies.SDS of cas: 79815-20-6 And the article contains the following content:

Since the discovery of endogenous nociceptin/orphanin FQ (N/OFQ) peptide and N/OFQ peptide (NOP) receptor [or opioid-receptor-like-1 (ORL1) receptor], the structures, distribution, and pharmacol. have been reported in detail. N/OFQ and NOP receptor are located in the corticolimbic regions that are involved in the integration of the emotional activity, and located in the spinal cord, the peripheral nervous systems or other peripheral tissues that are related to pain as well as urinary signal transmissions, with a pattern distinct from that of classical opioid peptides and their receptors in rodents or primates. Furthermore, N/OFQ-NOP receptor system plays an important role in the regulation of various human physiologies such as depression effect, hyperphasia effect, and blood pressure effect. In this study, the structure-activity relationship of novel NOP receptor antagonist for various 1-(β-amino substituted-β-alanyl)-N,N-dimethylindoline-2-carboxamides was investigated in vitro to elucidate structural requisites to identify and develop potent and selective NOP receptor antagonists, which resulted in the discovery of 1-{3-[4-(substituted phenyl)piperidin-1-yl]propanoyl}-N,N-dimethylindoline-2-carboxamide analogs that display potent and selective human NOP (hNOP) receptor binding affinity and potent hNOP receptor antagonist activity. The efficient design, synthesis, and structure-activity relationship studies for potent and selective novel NOP receptor antagonists and significant findings in vitro, that include insights for binding and functional mechanisms via receptor-ligand interactions, are reported herein. The experimental process involved the reaction of H-Idc-OH(cas: 79815-20-6).SDS of cas: 79815-20-6

The Article related to peptidomimetic synthesis nofq nop receptor antagonist structure activity pharmacokinetics, amino alanyl dimethylindoline carboxamide parallel synthesis metabolic stability lipophilicity, indoline carboxylic acid amidation amine michael addition drug design and other aspects.SDS of cas: 79815-20-6

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

On July 1, 2010, Suga, Hiroyuki; Arikawa, Tadashi; Itoh, Kennosuke; Okumura, Yukihisa; Kakehi, Akikazu; Shiro, Motoo published an article.Category: indole-building-block The title of the article was Asymmetric 1,3-dipolar cycloaddition reactions of azomethine imines with acrolein catalyzed by L-proline and its derivatives. And the article contained the following:

1,3-Dipolar cycloadditions between acrolein and various N,N’-cyclic azomethine imines in the presence of L-proline and its derivatives as organocatalysts were investigated. Reactions that were catalyzed by (S)-indoline-2-carboxylate (30 mol%) in CHCl3/MeOH 97:3 (volume/volume) showed high exo-selectivities (exo/endo 91:9∼99:1) and enantioselectivities (75∼98% ee). In contrast, reactions catalyzed by L-proline (30 mol%) under similar conditions favored the endo-cycloadduct (83:27∼99:1) with modest to good enantioselectivities (31∼83% ee). The diastereoselective mechanism of the L-proline-catalyzed reaction was found to involve the isomerization of the exo- to the endo-cycloadduct in the presence of L-proline. The experimental process involved the reaction of H-Idc-OH(cas: 79815-20-6).Category: indole-building-block

The Article related to azomethine imine acrolein asym dipolar cycloaddition proline catalyst, indolinecarboxylate catalyst asym dipolar cycloaddition azomethine imine acrolein, hydropyrazolopyrazole asym synthesis isomerization, pyrazolopyrazole hydro asym synthesis isomerization and other aspects.Category: indole-building-block

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

Li, Yunyun; Qi, Zisong; Wang, He; Yang, Xifa; Li, Xingwei published an article in 2016, the title of the article was Ruthenium(II)-Catalyzed C-H Activation of Imidamides and Divergent Couplings with Diazo Compounds: Substrate-Controlled Synthesis of Indoles and 3H-Indoles.Electric Literature of 65417-22-3 And the article contains the following content:

Indoles are an important structural motif that is commonly found in biol. active mols. In this work, conditions for divergent couplings between imidamides and acceptor-acceptor diazo compounds were developed that afforded NH indoles I (R = Et, Me, tbu, Bn, Ac; R1 = H, 5-Me, 5-Br, 4-F, 6-Cl, etc) and 3H-indoles II (R = Et, Me, tBu, Bn, ipr, allyl; R1 = H, 5-Cl, 5-tbu, 5-CN, 5,6-diCl, etc) under ruthenium catalysis. The coupling of α-diazoketoesters afforded NH indoles by cleavage of the C(N2)-C(acyl) bond whereas α-diazomalonates gave 3H-indoles by C-N bond cleavage. This reaction constitutes the first intermol. coupling of diazo substrates with arenes by ruthenium-catalyzed C-H activation. The experimental process involved the reaction of Methyl 2-methyl-1H-indole-3-carboxylate(cas: 65417-22-3).Electric Literature of 65417-22-3

The Article related to diazoketoester imidamide ruthenium activation annulation catalyst, nh indole preparation, diazomalonate imidamide ruthenium activation annulation catalyst, indole 3h preparation, c−h activation, diazo compounds, indoles, ruthenium, transition-metal catalysis and other aspects.Electric Literature of 65417-22-3

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

Galvan, Alicia; Calleja, Jonas; Gonzalez-Perez, Adan B.; Alvarez, Rosana; de Lera, Angel R.; Fananas, Francisco J.; Rodriguez, Felix published an article in 2015, the title of the article was Stereoselective [3+2] Carbocyclization of Indole-Derived Imines and Electron-Rich Alkenes: A Divergent Synthesis of Cyclopenta[b]indole or Tetrahydroquinoline Derivatives.Name: 1,5-Dimethyl-1H-indole-2-carbaldehyde And the article contains the following content:

An unprecedented stereoselective [3+2] carbocyclization reaction of indole-2-carboxaldehydes, anilines, and electron-rich alkenes to obtain cyclopenta[b]indoles is disclosed. This pathway is different from the well-established Povarov reaction: the formal [4+2] cycloaddition involving the same components, which affords tetrahydroquinolines. Moreover, by simply changing the Bronsted acid catalyst, this multicomponent coupling process could be divergently directed towards the conventional Povarov pathway to produce tetrahydroquinolines or to the new pathway (anti-Povarov) to generate cyclopenta[b]indoles. Supported by computational studies, a stepwise Mannich/Friedel-Crafts cascade is proposed for the new anti-Povarov reaction, whereas a concerted [4+2] cycloaddition mechanism is proposed for the Povarov reaction. The experimental process involved the reaction of 1,5-Dimethyl-1H-indole-2-carbaldehyde(cas: 883526-76-9).Name: 1,5-Dimethyl-1H-indole-2-carbaldehyde

The Article related to cyclopentaindole derivative stereoselective preparation, tetrahydroquinoline derivative stereoselective preparation, indolecarboxaldehyde arylamine dihydrofuran stereoselective carbocyclization, acid catalysis, divergent synthesis, heterocycles, indoles, synthetic methods and other aspects.Name: 1,5-Dimethyl-1H-indole-2-carbaldehyde

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