18/10/2022 - Indole Building Blocks

Schnute, Mark E’s team published research in Journal of Medicinal Chemistry in 2018-12-13 | 101083-92-5

Journal of Medicinal Chemistry published new progress about Autoimmune disease. 101083-92-5 belongs to class indole-building-block, and the molecular formula is C7H5N3O2, Recommanded Product: 5-Nitro-1H-pyrrolo[2,3-b]pyridine.

Schnute, Mark E.; Wennerstal, Mattias; Alley, Jennifer; Bengtsson, Martin; Blinn, James R.; Bolten, Charles W.; Braden, Timothy; Bonn, Tomas; Carlsson, Bo; Caspers, Nicole; Chen, Ming; Choi, Chulho; Collis, Leon P.; Crouse, Kimberly; Farnegardh, Mathias; Fennell, Kimberly F.; Fish, Susan; Flick, Andrew C.; Goos-Nilsson, Annika; Gullberg, Hjalmar; Harris, Peter K.; Heasley, Steven E.; Hegen, Martin; Hromockyj, Alexander E.; Hu, Xiao; Husman, Bolette; Janosik, Tomasz; Jones, Peter; Kaila, Neelu; Kallin, Elisabet; Kauppi, Bjorn; Kiefer, James R.; Knafels, John; Koehler, Konrad; Kruger, Lars; Kurumbail, Ravi G.; Kyne, Robert E.; Li, Wei; Lofstedt, Joakim; Long, Scott A.; Menard, Carol A.; Mente, Scot; Messing, Dean; Meyers, Marvin J.; Napierata, Lee; Noteberg, Daniel; Nuhant, Philippe; Pelc, Matthew J.; Prinsen, Michael J.; Rhonnstad, Patrik; Backstrom-Rydin, Eva; Sandberg, Johnny; Sandstrom, Maria; Shah, Falgun; Sjoberg, Maria; Sundell, Aron; Taylor, Alexandria P.; Thorarensen, Atli; Trujillo, John I.; Trzupek, John D.; Unwalla, Ray; Vajdos, Felix F.; Weinberg, Robin A.; Wood, David C.; Xing, Li; Zamaratski, Edouard; Zapf, Christoph W.; Zhao, Yajuan; Wilhelmsson, Anna; Berstein, Gabriel published the artcile< Discovery of 3-Cyano-N-(3-(1-isobutyrylpiperidin-4-yl)-1-methyl-4-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)benzamide: A Potent, Selective, and Orally Bioavailable Retinoic Acid Receptor-Related Orphan Receptor C2 Inverse Agonist>, Recommanded Product: 5-Nitro-1H-pyrrolo[2,3-b]pyridine, the main research area is cyanophenylamido isobutyrylpiperidinyl trifluoromethyl pyrrolopyridine preparation retinoic acid receptor; retinoic acid receptor related orphan receptor C2 inverse agonist; cyanobenzamide isobutyrylpiperidinyl pyrrolopyridinyl trifluoromethyl preparation retinoic acid receptor.

The nuclear hormone receptor retinoic acid receptor-related orphan C2 (RORC2, also known as RORγt) is a promising target for the treatment of autoimmune diseases. A small mol., inverse agonist of the receptor is anticipated to reduce production of IL-17, a key proinflammatory cytokine. Through a high-throughput screening approach, authors identified a mol. displaying promising binding affinity for RORC2, inhibition of IL-17 production in Th17 cells, and selectivity against the related RORA and RORB receptor isoforms. Lead optimization to improve the potency and metabolic stability of this hit focused on two key design strategies, namely, iterative optimization driven by increasing lipophilic efficiency and structure-guided conformational restriction to achieve optimal ground state energetics and maximize receptor residence time. This approach successfully identified 3-cyano-N-(3-(1-isobutyrylpiperidin-4-yl)-1-methyl-4-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)benzamide as a potent and selective RORC2 inverse agonist, demonstrating good metabolic stability, oral bioavailability, and the ability to reduce IL-17 levels and skin inflammation in a preclin. in vivo animal model upon oral administration.

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

Wang, Qing-Dong’s team published research in Synlett in 2017-12-31 | 4771-48-6

Synlett published new progress about Formylation, regioselective. 4771-48-6 belongs to class indole-building-block, and the molecular formula is C10H9NO, Related Products of 4771-48-6.

Wang, Qing-Dong; Zhou, Bin; Yang, Jin-Ming; Fang, Dong; Ren, Jiangmeng; Zeng, Bu-Bing published the artcile< Iron-Catalyzed C3-Formylation of Indoles with Formaldehyde and Aqueous Ammonia under Air>, Related Products of 4771-48-6, the main research area is formylindole preparation green chem regioselective; indole formaldehyde formylation iron catalyst.

An efficient iron-catalyzed C3-selective formylation of free (N-H) or N-substituted indoles such as 2-phenyl-1H-indole, 6-fluoro-1H-indole, 1-methyl-1H-indole, etc. was developed by employing formaldehyde and aqueous ammonia, with air as the oxidant. This new method gave 3-formylindoles such as 2-phenyl-1H-indole-3-carbaldehyde, 6-fluoro-1H-indole-3-carbaldehyde, 1-methyl-1H-indole-3-carbaldehyde, etc. in moderate to excellent yields with fairly short reaction times. Moreover, this procedure for catalytic formylation of indoles can be applied to gram-scale syntheses.

Synlett published new progress about Formylation, regioselective. 4771-48-6 belongs to class indole-building-block, and the molecular formula is C10H9NO, Related Products of 4771-48-6.

Sellmer, Andreas’s team published research in European Journal of Medicinal Chemistry in 2020-05-01 | 101083-92-5

European Journal of Medicinal Chemistry published new progress about Acute myeloid leukemia. 101083-92-5 belongs to class indole-building-block, and the molecular formula is C7H5N3O2, Reference of 101083-92-5.

Sellmer, Andreas; Pilsl, Bernadette; Beyer, Mandy; Pongratz, Herwig; Wirth, Lukas; Elz, Sigurd; Dove, Stefan; Henninger, Sven Julian; Spiekermann, Karsten; Polzer, Harald; Klaeger, Susan; Kuster, Bernhard; Boehmer, Frank D.; Fiebig, Heinz-Herbert; Kraemer, Oliver H.; Mahboobi, Siavosh published the artcile< A series of novel aryl-methanone derivatives as inhibitors of FMS-like tyrosine kinase 3 (FLT3) in FLT3-ITD-positive acute myeloid leukemia>, Reference of 101083-92-5, the main research area is aryl methanone preparation FLT3 tyrosine kinase inhibitor antitumor human; Acute myeloid leukemia; FLT3; FLT3 D835Y; FLT3-ITD; Tyrosine kinase inhibitor.

Mutants of the FLT3 receptor tyrosine kinase (RTK) with duplications in the juxtamembrane domain (FLT3-ITD) act as drivers of acute myeloid leukemia (AML). Potent tyrosine kinase inhibitors (TKi) of FLT3-ITD entered clin. trials and showed a promising, but transient success due to the occurrence of secondary drug-resistant AML clones. A further caveat of drugs targeting FLT3-ITD is the co-targeting of other RTKs which are required for normal hematopoiesis. This is observed quite frequently. Therefore, novel drugs are necessary to treat AML effectively and safely. Recently bis(1H-indol-2-yl)methanones were found to inhibit FLT3 and PDGFR kinases. In order to optimize these agents novel derivatives of these methanones with various substituents were synthesized. Methanone I and its carbamate derivative II inhibit FLT3-ITD at least as potently as the TKi AC220 (quizartinib). Models indicate corresponding interactions of I and quizartinib with FLT3. The activity of I is accompanied by a high selectivity for FLT3-ITD.

Chen, Weiliang’s team published research in Chemistry – A European Journal in 2015 | 4771-48-6

Chemistry – A European Journal published new progress about [3+2] Cycloaddition reaction. 4771-48-6 belongs to class indole-building-block, and the molecular formula is C10H9NO, Application In Synthesis of 4771-48-6.

Chen, Weiliang; Xia, Yong; Lin, Lili; Yuan, Xiao; Guo, Songsong; Liu, Xiaohua; Feng, Xiaoming published the artcile< Asymmetric Synthesis of Furo[3,4-b]indoles by Catalytic [3+2] Cycloaddition of Indoles with Epoxides>, Application In Synthesis of 4771-48-6, the main research area is indole furan furoindole preparation; N,N′-dioxide-metal complex; asymmetric synthesis; epoxides; indoles.

A highly efficient N,N’-dioxide-nickel(II) catalyst system for the catalytic [3+2] cycloaddition of indoles with epoxides through C-C cleavage of oxiranes (i.e., epoxides) was accomplished under mild conditions. It provided a promising approach for chiral furo[3,4-b]indoles in up to 98% yield with up to 91% enantiomeric excess (ee) and >95:5 diastereomeric ratio (d.r.). Under optimized conditions the synthesis of the target compounds was achieved using (1R,1’R,2S,2’S)-1,1′-(1,3-propanediyl)bis[N-[2,4,6-tris(1-methylethyl)phenyl]-2-pyrrolidinecarboxamide] 1,1′-dioxide, perchloric acid nickel(2+) salt hexahydrate (nickel perchlorate hexahydrate) and 1,1,1-trifluoro-N-[(trifluoromethyl)sulfonyl]methanesulfonamide lithium salt (lithium triflimide) as ligand-catalyst combination. Starting materials included 3-(4-methylphenyl)-2,2-oxiranedicarboxylic acid di-Me ester and 1,3-dimethyl-1H-indole derivatives The title compounds thus formed included 1,3a,4,8b-tetrahydro-4,8b-dimethyl-1-(4-methylphenyl)-3H-furo[3,4-b]indole-3,3-dicarboxylic acid 3,3-di-Me ester and related substances.

Pan, Changduo’s team published research in Organic & Biomolecular Chemistry in 2020 | CAS: 399-52-0

5-Fluoro-1H-indole(cas: 399-52-0) is a member of aromaticfluorinated building blocks. Fluorine-containing aromatics have been incorporated into crop-protection chemicals (herbicides, insecticides, fungicides). Liquid crystals, positron emission tomography, and imaging systems represent new areas where fluoroaromatics and fluoroheterocyclics have gained attention.Category: indole-building-block

《Rh(III)-Catalyzed regioselective C4 alkylation of indoles with allylic alcohols: direct access to β-indolyl ketones》 was published in Organic & Biomolecular Chemistry in 2020. These research results belong to Pan, Changduo; Huang, Gao; Shan, Yujia; Li, Yiting; Yu, Jin-Tao. Category: indole-building-block The article mentions the following:

A Rh(III)-catalyzed and weak coordination carbonyl guided direct C4 alkylation of indoles with allylic alcs. was developed with excellent regioselectivity. This reaction was conducted under mild conditions, leading to a variety of β-indolyl ketones with good functional group tolerance in moderate to good yields. In the experimental materials used by the author, we found 5-Fluoro-1H-indole(cas: 399-52-0Category: indole-building-block)

Plekan, Oksana’s team published research in Journal of Physical Chemistry A in 2020 | CAS: 120-72-9

1H-Indole(cas: 120-72-9) belongs to indole. Indole, also called Benzopyrrole, a heterocyclic organic compound occurring in some flower oils, such as jasmine and orange blossom, in coal tar, and in fecal matter. It is used in perfumery and in making tryptophan, an essential amino acid, and indoleacetic acid (heteroauxin), a hormone that promotes the development of roots in plant cuttings.Application In Synthesis of 1H-Indole

《Experimental and Theoretical Photoemission Study of Indole and Its Derivatives in the Gas Phase》 was written by Plekan, Oksana; Sa’adeh, Hanan; Ciavardini, Alessandra; Callegari, Carlo; Cautero, Giuseppe; Dri, Carlo; Di Fraia, Michele; Prince, Kevin C.; Richter, Robert; Sergo, Rudi; Stebel, Luigi; Devetta, Michele; Facciala, Davide; Vozzi, Caterina; Avaldi, Lorenzo; Bolognesi, Paola; Castrovilli, Mattea Carmen; Catone, Daniele; Coreno, Marcello; Zuccaro, Fabio; Bernes, Elisa; Fronzoni, Giovanna; Toffoli, Daniele; Ponzi, Aurora. Application In Synthesis of 1H-Indole And the article was included in Journal of Physical Chemistry A in 2020. The article conveys some information:

The valence and core-level photoelectron spectra of gaseous indole, 2,3-dihydro-7-azaindole, and 3-formylindole have been investigated using VUV and soft X-ray radiation supported by both an ab initio electron propagator and d. functional theory calculations Three methods were used to calculate the outer valence band photoemission spectra: outer valence Green function, partial third order, and renormalized partial third order. While all gave an acceptable description of the valence spectra, the last method yielded very accurate agreement, especially for indole and 3-formylindole. The carbon, nitrogen, and oxygen 1s core-level spectra of these heterocycles were measured and assigned. The double ionization appearance potential for indole has been determined to be 21.8 ± 0.2 eV by C 1s and N 1s Auger photoelectron spectroscopy. Theor. anal. identifies the doubly ionized states as a band consisting of two overlapping singlet states and one triplet state with dominant configurations corresponding to holes in the two uppermost MOs. One of the singlet states and the triplet state can be described as consisting largely of a single configuration, but other doubly ionized states are heavily mixed by configuration interactions. This work provides full assignment of the relative binding energies of the core level features and an anal. of the electronic structure of substituted indoles in comparison with the parent indole. The experimental process involved the reaction of 1H-Indole(cas: 120-72-9Application In Synthesis of 1H-Indole)

Antonov, Konstantin V.’s team published research in Carbohydrate Research in 1998 | CAS: 99409-32-2

Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranoside(cas: 99409-32-2) belongs to indole.The indole subunit is an almost ubiquitous component of biologically active natural products, and its study has been the focus of research for decades.Quality Control of Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranosideThey are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.

Antonov, Konstantin V.; Backinowsky, Leon V.; Grzeszczyk, Barbara; Brade, Lore; Holst, Otto; Zamojski, Aleksander published their research in Carbohydrate Research on December 21 ,1998. The article was titled 《Synthesis and serological characterization of L-glycero-α-D-manno-heptopyranose-containing di- and tri-saccharides of the non-reducing terminus of the Escherichia coli K-12 LPS core oligosaccharide》.Quality Control of Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranoside The article contains the following contents:

Synthesis of the title trisaccharide was accomplished by sugar chain extension starting from the non-reducing terminus: coupling of GlcpNAc with LD-Hepp, then adding Glcp-OAll. An alternative route started from the reducing end: coupling of LD-Hepp with Glcp-OAll, then addition of GlcpNAc. In the synthesis of the title disaccharide a modification of the first approach was employed. The allyl glycosides were coupled with cysteamine, activated with thiophosgene and conjugated to bovine serum albumin (BSA). The neoglycoconjugates obtained were used in immunochem. studies of monoclonal and polyclonal antibodies directed against Escherichia coli K-12 lipopolysaccharide.Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranoside(cas: 99409-32-2Quality Control of Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranoside) was used in this study.

El-Sokkary, Ramadan I.’s team published research in Carbohydrate Research in 1990 | CAS: 99409-32-2

Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranoside(cas: 99409-32-2) belongs to indole.The indole subunit is an almost ubiquitous component of biologically active natural products, and its study has been the focus of research for decades.Name: Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranosideThey are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.

El-Sokkary, Ramadan I.; Silwanis, Basim Azmy; Nashed, Mina A.; Paulsen, Hans published their research in Carbohydrate Research on August 15 ,1990. The article was titled 《Standardized intermediates for oligosaccharide synthesis: convenient preparation of 2-amino-2-deoxy-D-glucose derivatives and their conversion into the D-galactose analogs》.Name: Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranoside The article contains the following contents:

Treating tetraacetate I (R = Ac, NPhth = phthalimido) with allyl alc. in CH2Cl2 containing FeCl3 gave I (R = CH2:CHCH2O) which was deacetylated by NaOMe-MeOH followed by benzoylation with BzCl to give 95.8% phthalimido derivative II. The latter was treated with (CF3SO2)2O in CH2Cl2 to give an intermediate 4-triflate which was converted by NaNO2-DMF to 86% galactopyranoside III, a useful glycosyl donor for oligosaccharide synthesis. The results came from multiple reactions, including the reaction of Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranoside(cas: 99409-32-2Name: Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranoside)

Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranoside(cas: 99409-32-2) belongs to indole.The indole subunit is an almost ubiquitous component of biologically active natural products, and its study has been the focus of research for decades.Name: Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranosideThey are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.

Valerio, Silvia’s team published research in Journal of Organic Chemistry in 2007 | CAS: 99409-32-2

Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranoside(cas: 99409-32-2) belongs to indole.The indole subunit is an almost ubiquitous component of biologically active natural products, and its study has been the focus of research for decades.SDS of cas: 99409-32-2They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.

Valerio, Silvia; Iadonisi, Alfonso; Adinolfi, Matteo; Ravida, Alessandra published their research in Journal of Organic Chemistry on August 3 ,2007. The article was titled 《Novel Approaches for the Synthesis and Activation of Thio- and Selenoglycoside Donors》.SDS of cas: 99409-32-2 The article contains the following contents:

Alkyl thio-, Ph seleno-, and Ph thioglycosides can be prepared through short synthetic sequences based on the generation of glycosyl iodides as versatile intermediates. In addition, a novel cheap combined system (stoichiometric NBS and catalytic Bi(OTf)3) has been developed for rapid and efficient activation of a wide variety of thio- and selenoglycoside donors. After reading the article, we found that the author used Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranoside(cas: 99409-32-2SDS of cas: 99409-32-2)

Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranoside(cas: 99409-32-2) belongs to indole.The indole subunit is an almost ubiquitous component of biologically active natural products, and its study has been the focus of research for decades.SDS of cas: 99409-32-2They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.

Capretz Agy, Andre’s team published research in Journal of Organic Chemistry in 2019 | CAS: 399-52-0

In 2019,Journal of Organic Chemistry included an article by Capretz Agy, Andre; Rodrigues, Manoel T.; Zeoly, Lucas A.; Simoni, Deborah A.; Coelho, Fernando. Safety of 5-Fluoro-1H-indole. The article was titled 《Palladium-Mediated Oxidative Annulation of δ-Indolyl-α,β-Unsaturated Compounds toward the Synthesis of Cyclopenta[b]indoles and Heterogeneous Hydrogenation To Access Fused Indolines》. The information in the text is summarized as follows:

The cyclopenta[b]indole moiety represents a key skeletal unit in several natural and synthetic compounds that exhibit diverse biol. properties. We described herein a two-step sequence for synthesizing cyclopenta[b]indoles with great structural diversity in overall yields up to 37%. The key step was a palladium-catalyzed oxidative annulation of 3-alkylindoles (Fujiwara-Moritani reaction). The obtained cyclopenta[b]indoles were used as substrates in heterogeneous hydrogenation reactions to afford new fused indolines in moderate yields. An acid-catalyzed intramol. cyclization of three such indolines gave tetracyclic lactams in 89, 90, and 61% yields.5-Fluoro-1H-indole(cas: 399-52-0Safety of 5-Fluoro-1H-indole) was used in this study.