M.W=300-350 | - Page 4 of 4 - Indole Building Blocks

Zhang, Li’s team published research in Journal of the American Chemical Society in | CAS: 1206163-56-5

Journal of the American Chemical Society published new progress about 1206163-56-5. 1206163-56-5 belongs to indole-building-block, auxiliary class Indole,Boronic acid and ester,Benzene,Boronate Esters,Boronic Acids,Boronic acid and ester, name is 1-Benzyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole, and the molecular formula is C8H19NO, Safety of 1-Benzyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole.

Zhang, Li published the artcileVisible-Light-Induced Organocatalytic Borylation of Aryl Chlorides, Safety of 1-Benzyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole, the publication is Journal of the American Chemical Society, database is CAplus and MEDLINE.

The preparation of arylboronates from unactivated aryl chlorides in a transition-metal-free manner is rather challenging. There are only few examples to achieve this goal by using UV irradiation Based on the mechanistic understanding of the diboron/methoxide/pyridine reaction system, we achieved photoactivation of the in situ generated super electron donor and developed a visible-light-induced organocatalytic method for efficient borylation of unactivated aryl chlorides.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Chen, Wang’s team published research in Youji Huaxue in 34 | CAS: 149108-61-2

Youji Huaxue published new progress about 149108-61-2. 149108-61-2 belongs to indole-building-block, auxiliary class Indole,Boronic acid and ester,Sulfamide,Benzene,Boronic Acids,Boronic Acids,Boronic acid and ester,, name is (1-tosyl-1H-Indol-3-yl)boronic acid, and the molecular formula is C15H14BNO4S, Computed Properties of 149108-61-2.

Chen, Wang published the artcileSynthesis and antitumor activity of Lycogarubin C and Lycogalic acid, Computed Properties of 149108-61-2, the publication is Youji Huaxue (2014), 34(4), 797-803, database is CAplus.

Lycogarubin C and lycogalic acid were first isolated independently by Steglich and Akazawa from Lycogala epidendrum in 1994. Lycogarubin C showed a potential cytotoxic activity. Lycogalic acid is an inhibitor of Hes1 dimmer of helix-loop-helix (bHLH) transcriptional repressor factor. Lycogalic acid is also the key intermediate in the biosynthesis of indolo[2,3-a]carbazole alkaloids that exhibit broad spectrum of bioactivity. Two efficient synthetic pathways of lycogarubin C and lycogalic acid were completed in this study. The first pathway included eight steps started from the com. available indole and pyrrole to produce lycogarubin C with an overall yield of 27%. The second pathway was completed in seven steps with an overall yield of 25%. The key reactions are palladium-catalyzed Suzuki-Miyaura coupling of bis-iodo or bis-triflate derivative and indolboronic acid derivatives and Hinsberg-type synthesis of di-Me N-benzyl-3,4-dihydroxypyrrole-2,5-dicarboxylate, resp. Treatment of lycogarubin C with sodium hydroxide in ethanol under refluxing followed by acidification afforded lycogalic acid quant. Lycogarubin C and lycogalic acid showed the antiproliferative activities against four human tumor cell lines of MDA-MB-231, A549, HeLa and PC3. Further study showed that lycogarubin C inhibited the activity of DNA topoisomerase 2.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Landstrom, Evan B.’s team published research in Green Chemistry in 20 | CAS: 480438-51-5

Green Chemistry published new progress about 480438-51-5. 480438-51-5 belongs to indole-building-block, auxiliary class Indole,Boronic acid and ester,Sulfamide,Benzene,Boronic Acids,Boronic Acids,Boronic acid and ester,, name is (1-(Phenylsulfonyl)-1H-indol-5-yl)boronic acid, and the molecular formula is C14H12BNO4S, SDS of cas: 480438-51-5.

Landstrom, Evan B. published the artcileEvanPhos: a ligand for ppm level Pd-catalyzed Suzuki-Miyaura couplings in either organic solvent or water, SDS of cas: 480438-51-5, the publication is Green Chemistry (2018), 20(15), 3436-3443, database is CAplus.

A new biaryl phosphine-containing palladium complex was constructed and its usefulness in Suzuki-Miyaura cross-couplings of functionalized substrates so as to yield biaryls was evaluated. By a combination of pre-activation using DIBAL and employment of uncommon solvent EtOAc, the novel catalyst proved effective with extended bench stability at loadings in the ppm (0.1-0.5 mol%) range with highly functionalized reaction partners. Similar reactions run in water containing nanomicelles were as fast or faster. This methodol. represented an attractive green synthetic advance in highly valued Suzuki-Miyaura couplings.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Landstrom, Evan B.’s team published research in Green Chemistry in 20 | CAS: 149108-61-2

Green Chemistry published new progress about 149108-61-2. 149108-61-2 belongs to indole-building-block, auxiliary class Indole,Boronic acid and ester,Sulfamide,Benzene,Boronic Acids,Boronic Acids,Boronic acid and ester,, name is (1-tosyl-1H-Indol-3-yl)boronic acid, and the molecular formula is C15H14BNO4S, COA of Formula: C15H14BNO4S.

Landstrom, Evan B. published the artcileEvanPhos: a ligand for ppm level Pd-catalyzed Suzuki-Miyaura couplings in either organic solvent or water, COA of Formula: C15H14BNO4S, the publication is Green Chemistry (2018), 20(15), 3436-3443, database is CAplus.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Lou, Sha’s team published research in Advanced Synthesis & Catalysis in 352 | CAS: 149108-61-2

Advanced Synthesis & Catalysis published new progress about 149108-61-2. 149108-61-2 belongs to indole-building-block, auxiliary class Indole,Boronic acid and ester,Sulfamide,Benzene,Boronic Acids,Boronic Acids,Boronic acid and ester,, name is (1-tosyl-1H-Indol-3-yl)boronic acid, and the molecular formula is C15H14BNO4S, COA of Formula: C15H14BNO4S.

Lou, Sha published the artcilePalladium/Tris(tert-butyl)phosphine-Catalyzed Suzuki Cross- Couplings in the Presence of Water, COA of Formula: C15H14BNO4S, the publication is Advanced Synthesis & Catalysis (2010), 352(11+12), 2081-2084, database is CAplus and MEDLINE.

The use of dipalladiumtris(dibenzylideneacetone)/tris(tert-butyl)phosphonium tetrafluoroborate/potassium fluoride dihydrate [Pd₂(dba)₃/[HP(t-Bu)₃]BF₄/KF·2 H₂O] as a mild, robust, and user-friendly method for the efficient Suzuki cross-coupling of a diverse array of aryl and heteroaryl halides with aryl- and heteroarylboronic acids is demonstrated.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Wang, Pingyuan’s team published research in ACS Medicinal Chemistry Letters in 10 | CAS: 837392-67-3

ACS Medicinal Chemistry Letters published new progress about 837392-67-3. 837392-67-3 belongs to indole-building-block, auxiliary class Indoline,Boronic acid and ester,Amide,Boronate Esters,Aliphatic Heterocyclic, name is tert-Butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indoline-1-carboxylate, and the molecular formula is C19H21N3O, Product Details of C19H28BNO4.

Wang, Pingyuan published the artcileSynthesis and Pharmacological Evaluation of Noncatechol G Protein Biased and Unbiased Dopamine D1 Receptor Agonists, Product Details of C19H28BNO4, the publication is ACS Medicinal Chemistry Letters (2019), 10(5), 792-799, database is CAplus and MEDLINE.

Noncatechol heterocycles have recently been discovered as potent and selective G protein biased dopamine 1 receptor (D1R) agonists with superior pharmacokinetic properties. To determine the structure-activity relations centered on G protein or β-arrestin signaling bias, systematic medicinal chem. was employed around three aromatic pharmacophores of the lead compound PF2334, generating a series of new mols. that were evaluated at both D1R G_s-dependent cAMP signaling and β-arrestin recruitment in HEK293 cells. Here, the authors report the chem. synthesis, pharmacol. evaluation, and mol. docking studies leading to the identification of two novel noncatechol D1R agonists that are a subnanomolar potent unbiased ligand 6-(4-(Furo[3,2-c]pyridin-4-yloxy)-2-methylphenyl)-1,5-dimethylpyrimidine-2,4(1H,3H)dione (PW0441) and a nanomolar potent complete G protein biased ligand 6-(4-((3-(Difluoromethoxy)pyridin-2-yl)oxy)-2-methylphenyl)-1,5-dimethylpyrimidine-2,4(1H,3H)-dione (PW0464), resp. These novel D1R agonists provide important tools to study D1R activation and signaling bias in both health and disease.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Achab, Said’s team published research in Tetrahedron Letters in 42 | CAS: 149108-61-2

Tetrahedron Letters published new progress about 149108-61-2. 149108-61-2 belongs to indole-building-block, auxiliary class Indole,Boronic acid and ester,Sulfamide,Benzene,Boronic Acids,Boronic Acids,Boronic acid and ester,, name is (1-tosyl-1H-Indol-3-yl)boronic acid, and the molecular formula is C15H14BNO4S, Product Details of C15H14BNO4S.

Achab, Said published the artcileA short route to functionalized imidazo[4,5-c]carbazoles. Synthesis of the first example of the imidazo[4,5-c]β-carboline ring system, Product Details of C15H14BNO4S, the publication is Tetrahedron Letters (2001), 42(50), 8825-8828, database is CAplus.

A new synthetic route to the functionalized imidazo[4,5-c]carbazole I, via intramol. electrocyclization of the vinylimidazolylindole II is described. Thermally induced ring-closure of the (4-amino-5-imidazolyl)-3-indolecarboxylate III led to the previously unknown imidazo[4,5-c]-β-carboline ring system IV. These heterocycles were efficiently converted into analogs of both the marine cytotoxic agents grossularines-1 and -2 and the antimicrobial alkaloid eudistomin U.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Tsai, Henry J.’s team published research in Journal of Biomedical Science (London, United Kingdom) in 16 | CAS: 149108-61-2

Journal of Biomedical Science (London, United Kingdom) published new progress about 149108-61-2. 149108-61-2 belongs to indole-building-block, auxiliary class Indole,Boronic acid and ester,Sulfamide,Benzene,Boronic Acids,Boronic Acids,Boronic acid and ester,, name is (1-tosyl-1H-Indol-3-yl)boronic acid, and the molecular formula is C6H12F3NO5S, Safety of (1-tosyl-1H-Indol-3-yl)boronic acid.

Tsai, Henry J. published the artcileA novel hydroxyfuroic acid compound as an insulin receptor activator – structure and activity relationship of a prenylindole moiety to insulin receptor activation, Safety of (1-tosyl-1H-Indol-3-yl)boronic acid, the publication is Journal of Biomedical Science (London, United Kingdom) (2009), No pp. given, database is CAplus and MEDLINE.

Background: Diabetes Mellitus is a chronic disease and many patients of which require frequent s.c. insulin injection to maintain proper blood glucose levels. Due to the inconvenience of insulin administration, an orally active insulin replacement has long been a prime target for many pharmaceutical companies. Demethylasterriquinone (DMAQ) B1, extracted from tropical fungus, Pseudomassaria sp., has been reported to be an orally effective agent at lowering circulating glucose levels in diabetic (db/db) mice; however, the cytotoxicity associated with the quinone moiety has not been addressed thus far. Methods: A series of hydroxyfuroic acid compounds were synthesized and tested for their efficacies at activating human insulin receptor. Cytotoxicity to Chinese hamster ovary cells, selectivities over insulin-like growth factor-1 (IGF-1), epidermal growth factor (EGF), and fibroblast growth factor (FGF) receptors were examined in this study. Results and conclusions: This study reports a new non-quinone DMAQ B1 derivative, a hydroxyfuroic acid compound (D-410639), which is 128 fold less cytotoxic as DMAQ B1 and as potent as compound 2, a DMAQ B1 synthetic derivative from Merck, at activating human insulin receptor. D-410639 has little activation potential on IGF-1 receptor but is a moderate inhibitor to EGF receptor. Structure and activity relationship of the prenylindole moiety to insulin receptor activation is discussed.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Xu, Jinhui’s team published research in Journal of the American Chemical Society in 143 | CAS: 1206163-56-5

Xu, Jinhui published the artcileUnveiling Extreme Photoreduction Potentials of Donor-Acceptor Cyanoarenes to Access Aryl Radicals from Aryl Chlorides, Synthetic Route of 1206163-56-5, the publication is Journal of the American Chemical Society (2021), 143(33), 13266-13273, database is CAplus and MEDLINE.

Since the seminal work of Zhang in 2016, donor-acceptor cyanoarene-based fluorophores, such as 1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene (4CzIPN), have been widely applied in photoredox catalysis and used as excellent metal-free alternatives to noble metal Ir- and Ru-based photocatalysts. However, all the reported photoredox reactions involving this chromophore family are based on harnessing the energy from a single visible light photon, with a limited range of redox potentials from -1.92 to +1.79 V vs SCE. Here, we document the unprecedented discovery that this family of fluorophores can undergo consecutive photoinduced electron transfer (ConPET) to achieve very high reduction potentials. One of the newly synthesized catalysts, 2,4,5-tri(9H-carbazol-9-yl)-6-(ethyl(phenyl)amino)isophthalonitrile (3CzEPAIPN), possesses a long-lived (12.95 ns) excited radical anion form, 3CzEPAIPN^â?*, which can be used to activate reductively recalcitrant aryl chlorides (E_red â?-1.9 to -2.9 V vs SCE) under mild conditions. The resultant aryl radicals can be engaged in synthetically valuable aromatic C-B, C-P, and C-C bond formation to furnish arylboronates, arylphosphonium salts, arylphosphonates, and spirocyclic cyclohexadienes.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Nakamura, Hideshi’s team published research in Tetrahedron Letters in 41 | CAS: 149108-61-2

Nakamura, Hideshi published the artcileConvergent and short-step syntheses of dl-Cypridina luciferin and its analogs based on Pd-mediated cross couplings, Safety of (1-tosyl-1H-Indol-3-yl)boronic acid, the publication is Tetrahedron Letters (2000), 41(13), 2185-2188, database is CAplus.

(±)-Cypridina luciferin and its analogs I (X = NH, O, S) were synthesized from 2-aminopyrazine by an eight-step method that included two regio-selective Pd-mediated cross couplings, and their chemi- and bioluminescent activities were compared. Analogs having a 3-benzofuranyl or a 3-benzothienyl group in the place of a 3-indolyl group showed luciferase affinities similar to Cypridina luciferase but with a lower luminescent efficiency, suggesting that the NH group is unimportant for mol. recognition whereas the indolyl group is crucial for efficient luminescence.

Referemce:
https://www.nature.com/articles/s41429-020-0333-2,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles