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Lin, Cai et al. published their research in Journal of Medicinal Chemistry in 2019 | CAS: 1000340-39-5

3-Bromo-4-chloro-7-azaindole (cas: 1000340-39-5) belongs to indole derivatives. In addition to tryptophan, indigo, and indoleacetic acid, numerous compounds obtainable from plant or animal sources contain the indole molecular structure. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Safety of 3-Bromo-4-chloro-7-azaindole

Discovery of Pyrrolo[2,3-b]pyridine (1,7-Dideazapurine) Nucleoside Analogues as Anti-Trypanosoma cruzi Agents was written by Lin, Cai;Hulpia, Fabian;da Silva, Cristiane Franca;Batista, Denise da Gama Jaen;Van Hecke, Kristof;Maes, Louis;Caljon, Guy;Soeiro, Maria de Nazare C.;Van Calenbergh, Serge. And the article was included in Journal of Medicinal Chemistry in 2019.Safety of 3-Bromo-4-chloro-7-azaindole This article mentions the following:

Trypanosoma cruzi is the causative pathogen of Chagas disease and the main culprit for cardiac-related mortality in Latin-America triggered by an infective agent. Incapable of synthesizing purines de novo, this parasite depends on acquisition and processing of host-derived purines, making purine (nucleoside) analogs a potential source of antitrypanosomal agents. In this respect, hitherto 7-deazaadenosine (tubercidin) analogs attracted most attention. Here, we investigated analogs with an addnl. nitrogen (N1) removed. Structure-activity relationship investigation showed that C7 modification afforded analogs with potent antitrypanosomal activity. Halogens and small, linear carbon-based substituents were preferred. Compound 11 proved most potent in vitro, showed full suppression of parasitemia in a mouse model of acute infection, and elicited 100% animal survival after oral dosing at 25 mg/kg b.i.d. for 5 and 15 days. Cyclophosphamide-induced immunosuppression led to recrudescence. Washout experiments demonstrated a lack of complete clearance of infected cell cultures, potentially explaining the in vivo results. In the experiment, the researchers used many compounds, for example, 3-Bromo-4-chloro-7-azaindole (cas: 1000340-39-5Safety of 3-Bromo-4-chloro-7-azaindole).

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

Denmark, Scott E. et al. published their research in Journal of Organic Chemistry in 2017 | CAS: 14204-27-4

2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4) belongs to indole derivatives. Indole, first isolated in 1866, and it is commonly synthesized from phenylhydrazine and pyruvic acid, although several other procedures have been discovered. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Related Products of 14204-27-4

Catalytic, Enantioselective, Intramolecular Sulfenofunctionalization of Alkenes with Phenols was written by Denmark, Scott E.;Kornfilt, David J. P.. And the article was included in Journal of Organic Chemistry in 2017.Related Products of 14204-27-4 This article mentions the following:

The catalytic, enantioselective, cyclization of phenols with electrophilic sulfenophthalimides onto isolated or conjugated alkenes affords 2,3-disubstituted benzopyrans, e.g., I, and benzoxepins. The reaction is catalyzed by a BINAM-based phosphoramide Lewis base catalyst which assists in the highly enantioselective formation of a thiiranium ion intermediate. The influence of nucleophile electron d., alkene substitution pattern, tether length and Lewis base functional groups on the rate, enantio- and site-selectivity for the cyclization is investigated. The reaction is not affected by the presence of substituents on the phenol ring. In contrast, substitutions around the alkene strongly affect the reaction outcome. Sequential lengthening of the tether results in decreased reactivity, which necessitated increased temperatures for reaction to occur. Sterically bulky aryl groups on the sulfenyl moiety prevented erosion of enantiomeric composition at these elevated temperatures Alcs. and carboxylic acids preferentially captured thiiranium ions in competition with phenolic hydroxyl groups. An improved method for the selective C(2) allylation of phenols is also described. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4Related Products of 14204-27-4).

Grimm, Sebastian H. et al. published their research in Bioorganic & Medicinal Chemistry in 2019 | CAS: 754214-56-7

7-Azaindole-5-boronic Acid Pinacol Ester (cas: 754214-56-7) belongs to indole derivatives. 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. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.SDS of cas: 754214-56-7

Comprehensive structure-activity-relationship of azaindoles as highly potent FLT3 inhibitors was written by Grimm, Sebastian H.;Gagestein, Berend;Keijzer, Jordi F.;Liu, Nora;Wijdeven, Ruud H.;Lenselink, Eelke B.;Tuin, Adriaan W.;van den Nieuwendijk, Adrianus M. C. H.;van Westen, Gerard J. P.;van Boeckel, Constant A. A.;Overkleeft, Herman S.;Neefjes, Jacques;van der Stelt, Mario. And the article was included in Bioorganic & Medicinal Chemistry in 2019.SDS of cas: 754214-56-7 This article mentions the following:

Acute myeloid leukemia (AML) is characterized by fast progression and low survival rates, in which Fms-like tyrosine kinase 3 (FLT3) receptor mutations have been identified as a driver mutation in cancer progression in a subgroup of AML patients. Clin. trials have shown emergence of drug resistant mutants, emphasizing the ongoing need for new chem. matter to enable the treatment of this disease. Here, we present the discovery and topol. structure-activity relationship (SAR) study of analogs of isoquinolinesulfonamide H-89, a well-known PKA inhibitor, as FLT3 inhibitors. Surprisingly, we found that the SAR was not consistent with the observed binding mode of H-89 in PKA. Matched mol. pair anal. resulted in the identification of highly active sub-nanomolar azaindoles as novel FLT3-inhibitors. Structure based modeling using the FLT3 crystal structure suggested an alternative, flipped binding orientation of the new inhibitors. In the experiment, the researchers used many compounds, for example, 7-Azaindole-5-boronic Acid Pinacol Ester (cas: 754214-56-7SDS of cas: 754214-56-7).

Barltrop, J. A. et al. published their research in Journal of the Chemical Society in 1954 | CAS: 16732-64-2

4-Bromo-1H-indole-2-carboxylic acid (cas: 16732-64-2) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Category: indole-building-block

Synthesis of lysergic acid. I. Derivatives of indole was written by Barltrop, J. A.;Taylor, D. A. H.. And the article was included in Journal of the Chemical Society in 1954.Category: indole-building-block This article mentions the following:

As a model for the synthesis of lysergic acid, 2-methyl-3(2-oxocyclohexylidenemethyl)indole (I), prepared by condensing 2-methylindole (II) with formylcyclohexanone (III), was reduced to 2-methyl-3-(2-oxocyclohexylmethyl)indole (IV) and cyclized in small yield to a tetracyclic system (V), 4,6,6a,7,8,9-or 4,6,7,8,9,10-hexahydro-5-methyldibenz[cd,f] isoindole. An alternative, involving the cyclization of 4-bromo-3(2-oxocyclohexylmethyl)indole by an intramol. Grignard reaction, failed since the essential intermediate, 4-bromoindole (VI), could not be prepared II (9.5 g.) and 20 g. III in EtOH refluxed 2 h. gave 10 g. I, yellow prisms, m. 126° (from EtOH); dinitrophenylhydrazone, orange needles, m. 234°. I (0.67 g.) in EtOH hydrogenated at room temperature and pressure over Pd-C 1 h. gave IV, a colorless oil; picrate, m. 135° (from C₆H₆); semicarbazone, plates, m. 199-200° (decomposition). Indole (2 g.) and 4 g. III refluxed 2 h. in EtOH also gave 3-(2-oxocyclohexylidenemethyl)indole, needles, m. 232°. 2-Phenylindole and III in EtOH gave a blue substance, m. 200°, which is apparently of complex structure. IV (1 g.) was stirred 2 min. at 130° in 4 g. P₂O₅ and 3 cc. sirupy H₃PO₄, the insoluble residue dissolved in MeOH, the solution brought to pH 6, 2 g. Girard’s reagent “P” added, and the solution refluxed 20 min. The residue yielded the picrate of V, red needles, m. 144°. When 9.3 g. IV in 50 cc. PhMe was refluxed 1 h. with P₂O₅ no ketone fraction could be isolated. 2,6-Br(O₂N)C₆H₃Me (VII) (1 kg. crude), recrystallized, yielded 400 g. pure VII, m. 42°, and 500 g. 4,2-Br(O₂N)C₆H₃Me (VIII), m. 47°. VII (216 g.) and 143 g. (CO₂Et)₂, refluxed 45 min. with NaOEt in EtOH give 119 g. 2,6-Br(O₂N)C₆H₃CH₂COCO₂H (IX), m. 117° (from C₆H₆); semicarbazone, m. 216°. From the steam distillate was recovered 115 g. VII. Similarly VIII gave 40% 4,2-Br(O₂N)C₆H₃CH₂COCO₂H (X), needles, m. 144°, and 51% unchanged VIII. IX (28 g.) reduced in a refluxing solution of 150 g. FeSO₄.7H₂O and 60 cc. NH₄OH in 600 cc. H₂O 5 min. gave 18 g. 4-bromo-2-indolecarboxylic acid (XI), m. 266° (from EtOH). IX (28 g.) and 45 cc. 10% NaOH in 100 cc. H₂O treated during 1 h. with 53 g. Na₂S₂O₄, and the solution acidified with HCl and heated 2 h. gives 22 g. XI. Similarly X gave the 6-Br isomer of XI, needles, m. 223° (from aqueous EtOH). VII (21.6 g.) suspended in 50 cc. EtOH, hydrogenated with Raney Ni at room temperature and 3 atm. pressure, gave 17 g. 6,2-Br(H₂N)C₆H₃Me (XII), b₁₆ 130°. XII (9.3 g.) heated overnight in 20 cc. anhydrous HCO₂H gave 10 g. N-formyl derivative, (XIII), leaflets, m. 116°. 4,2-Br(HCONH)C₆H₃Me, needles, m. 137°, was similarly prepared from VIII. XIII (16 g.) added to 2.9 g. K in 100 cc. tert-BuOH, the alc. distilled, and the residue heated 0.5 h. to 270° did not form any VI. 6,2-Br(AcNH)C₆H₃Me (34 g.) warmed under N with 14 g. NaNH₂ until evolution of NH₃ ceased, then heated 15 min. at 240°, did not afford 4-bromo-2-methylindole. Me 2-bromocinnamate (11.4 g.) in concentrated H₂SO₄ treated during 0.5 h. at 0° with 3.5 g. HNO₃ (d. 1.48) in 10 cc. H₂SO₄ gave 13.7 g. crude product which, triturated with MeOH, yielded 9.5 g. Me 2-bromo-5-nitrocinnamate (XIV), yellow needles, m. 169° (from MeOH). XIV (6 g.) suspended in 50% H₂SO₄ and refluxed a few min. with a saturated solution of 7 g. KMnO₄ gave 2.4 g. 2,5-Br(O₂N)C₆H₃Me, needles, m. 178° (from aqueous EtOH). In the experiment, the researchers used many compounds, for example, 4-Bromo-1H-indole-2-carboxylic acid (cas: 16732-64-2Category: indole-building-block).

Khalafy, Jabbar et al. published their research in Australian Journal of Chemistry in 1998 | CAS: 5388-42-1

2-Phenylisoindolin-1-one (cas: 5388-42-1) belongs to indole derivatives. 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. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.HPLC of Formula: 5388-42-1

Flash vacuum pyrolysis of some N-benzylbenzotriazoles and N-benzylbenzisoxazolones was written by Khalafy, Jabbar;Prager, Rolf H.. And the article was included in Australian Journal of Chemistry in 1998.HPLC of Formula: 5388-42-1 This article mentions the following:

The flash vacuum pyrolysis products of 2-(benzotriazol-1-ylmethyl)benzonitrile, Me 2-(benzotriazol-1-ylmethyl)benzoate, and the corresponding benzisoxazolones have been characterized. The benzotriazoles lose nitrogen to give diradicals, which undergo intramol. hydrogen-atom transfer or cyclization, while the benzisoxazolones rearrange initially to the corresponding benzaldehyde N-(2-carboxyphenyl)imines, which undergo subsequent intramol. addition reactions. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1HPLC of Formula: 5388-42-1).

Zou, Zirong et al. published their research in Journal of Organic Chemistry in 2021 | CAS: 5388-42-1

2-Phenylisoindolin-1-one (cas: 5388-42-1) belongs to indole derivatives. Indole, first isolated in 1866, and it is commonly synthesized from phenylhydrazine and pyruvic acid, although several other procedures have been discovered. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Reference of 5388-42-1

Metal-Free Cascade Formation of Intermolecular C-N Bonds Accessing Substituted Isoindolinones under Cathodic Reduction was written by Zou, Zirong;Cai, Genuo;Chen, Weihao;Zou, Canlin;Li, Yamei;Wu, Hongting;Chen, Lu;Hu, Jinhui;Li, Yibiao;Huang, Yubing. And the article was included in Journal of Organic Chemistry in 2021.Reference of 5388-42-1 This article mentions the following:

An electrochem. protocol for the construction of substituted isoindolinones I (R¹ = H, 5-Me, 6-Cl, etc.; R² = Ph, c-hexyl, 2-furyl, etc.) via reduction/amidation of 2-carboxybenzaldehydes and amines has been realized. Under metal-free and external-reductant-free electrolytic conditions, the reaction achieves the cascade formation of intermol. C-N bonds and provides a series of isoindolinones in moderate to good yields. The deuterium-labeling experiment proves that the hydrogen in the methylene of the product is mainly provided by H2O in the system. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Reference of 5388-42-1).

Smith, Steven et al. published their research in ACS Omega in 2017 | CAS: 754214-56-7

7-Azaindole-5-boronic Acid Pinacol Ester (cas: 754214-56-7) belongs to indole derivatives. Indole is an important structural motif of various drugs, therapeutic leads besides its prevalence in numerous natural products, agrochemicals, perfumery, and dyes. Indole plays a fundamental role for QS in E. coli, being one of the signal molecules responsible for the transcription of a variety of genes (gabT, and tnaB ASTD). Formula: C13H17BN2O2

Characterization of Covalent-Reversible EGFR Inhibitors was written by Smith, Steven;Keul, Marina;Engel, Julian;Basu, Debjit;Eppmann, Simone;Rauh, Daniel. And the article was included in ACS Omega in 2017.Formula: C13H17BN2O2 This article mentions the following:

Within the spectrum of kinase inhibitors, covalent-reversible inhibitors (CRIs) provide a valuable alternative approach to classical covalent inhibitors. This special class of inhibitors can be optimized for an extended drug-target residence time. For CRIs, it was shown that the fast addition of thiols to electron-deficient olefins leads to a covalent bond that can break reversibly under proteolytic conditions. Research groups are just beginning to include CRIs in their arsenal of compound classes, and, with that, the understanding of this interesting set of chem. warheads is growing. However, systems to assess both characteristics of the covalent-reversible bond in a simple exptl. setting are sparse. Here, we have developed an efficient methodol. to characterize the covalent and reversible properties of CRIs and to investigate their potential in targeting clin. relevant variants of the receptor tyrosine kinase EGFR. In the experiment, the researchers used many compounds, for example, 7-Azaindole-5-boronic Acid Pinacol Ester (cas: 754214-56-7Formula: C13H17BN2O2).

Takahashi, Ichiro et al. published their research in Heterocycles in 2019 | CAS: 5388-42-1

2-Phenylisoindolin-1-one (cas: 5388-42-1) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.COA of Formula: C14H11NO

Exploration of moderate conditions and substrate variation in the direct condensation between phthalide and primary amine catalyzed by GaCl₃. Are aliphatic amines less reactive than aromatic ones? was written by Takahashi, Ichiro;Nishiwaki, Yoshinori;Saitoh, Kenta;Matsunaga, Takatoshi;Aratake, Akihiro;Morita, Toshio;Hosoi, Shinzo. And the article was included in Heterocycles in 2019.COA of Formula: C14H11NO This article mentions the following:

Direct condensation between phthalide and primary amines RNH₂ (R = n-Bu, 2-nitrophenyl, naphthalen-2-yl, etc.) in the presence of Lewis acid was achieved for the first time in organic solvent-diluted reaction systems catalyzed by GaCl₃. The peripheral aspect of this reaction is discussed. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1COA of Formula: C14H11NO).

Bao, Xiaoze et al. published their research in Organic Letters in 2015 | CAS: 14204-27-4

2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4) belongs to indole derivatives. Indole is an important structural motif of various drugs, therapeutic leads besides its prevalence in numerous natural products, agrochemicals, perfumery, and dyes. 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.Product Details of 14204-27-4

An Organocatalytic Asymmetric Friedel-Crafts Addition/Fluorination Sequence: Construction of Oxindole-Pyrazolone Conjugates Bearing Vicinal Tetrasubstituted Stereocenters was written by Bao, Xiaoze;Wang, Baomin;Cui, Longchen;Zhu, Guodong;He, Yuli;Qu, Jingping;Song, Yuming. And the article was included in Organic Letters in 2015.Product Details of 14204-27-4 This article mentions the following:

A highly efficient and practical one-pot sequential process, consisting of an organocatalytic enantioselective Friedel-Crafts-type addition of 4-nonsubstituted pyrazolones to isatin-derived N-Boc ketimines and a subsequent diastereoselective fluorination of the pyrazolone moiety, is developed. This reaction sequence delivers novel oxindole-pyrazolone adducts featuring vicinal tetrasubstituted stereocenters with a 0.5 mol % catalyst loading in high yield with excellent enantio- and diastereocontrol. Notably, chloro, bromo, and thioether functionalities can be readily incorporated, rendering a broad diversity of the product. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4Product Details of 14204-27-4).

Stenlid, Goeran et al. published their research in Physiologia Plantarum in 1987 | CAS: 1912-45-4

2-(5-Chloro-1H-indol-3-yl)acetic acid (cas: 1912-45-4) belongs to indole derivatives. 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.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Recommanded Product: 2-(5-Chloro-1H-indol-3-yl)acetic acid

Effects of chlorosubstituted indoleacetic acids on root growth, ethylene and ATP formation was written by Stenlid, Goeran;Engvild, Kjeld C.. And the article was included in Physiologia Plantarum in 1987.Recommanded Product: 2-(5-Chloro-1H-indol-3-yl)acetic acid This article mentions the following:

7-Chloroindoleacetic acid and dichloroindoleacetic acids with a Cl in the 7 position showed anti-auxinic activity and promoted root growth in wheat (Triticum aestivum c. Diamant II). In contrast, 4-, 5-, and 6-chloroindoleacetic acids acted as strong auxins inhibiting the growth of wheat roots. Flax (Linum usitatissimum cv. Conconcurrent) and cucumber (Cucumis sativus cv. Favr̈) roots showed similar, but less clear-cut responses. 7-Chloroindoleacetic acid and 4,7-dichloroindoleacetic acid alleviated root growth inhibition in wheat caused by IAA, monochloroindoleacetic acids, and benzyladenine. 2,4-D, and 4-, and 6-chloroindoleacetic acids strongly induced ethylene formation in cucumber seedlings; 4,7- and 6,7-dichloroindoleacetic acids did not, except at high concentrations The more lipid-soluble dichloroindoleacetic acids were stronger inhibitors of ATP formation in cucumber mitochondria than monochloroindoleacetic acids, while IAA itself had only a very slight effect. In the experiment, the researchers used many compounds, for example, 2-(5-Chloro-1H-indol-3-yl)acetic acid (cas: 1912-45-4Recommanded Product: 2-(5-Chloro-1H-indol-3-yl)acetic acid).