20/02/2023 - Page 5 of 14 - Indole Building Blocks

Adam, Rosa et al. published their research in Angewandte Chemie, International Edition in 2016 | CAS: 5388-42-1

2-Phenylisoindolin-1-one (cas: 5388-42-1) 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. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Application of 5388-42-1

Esters, Including Triglycerides, and Hydrogen as Feedstocks for the Ruthenium-Catalyzed Direct N-Alkylation of Amines was written by Adam, Rosa;Cabrero-Antonino, Jose R.;Junge, Kathrin;Jackstell, Ralf;Beller, Matthias. And the article was included in Angewandte Chemie, International Edition in 2016.Application of 5388-42-1 This article mentions the following:

Triglycerides are used for the direct N-alkylation of amines with mol. hydrogen for the first time. A broad range of interesting and industrially relevant secondary and tertiary amines are obtained in the presence of an in situ formed Ru/Triphos complex. Notably, plant oil can be efficiently applied in this single-step process. Moreover, a variety of other Me esters can be used as N-alkylation agents in the presence of hydrogen for the synthesis of more advanced building blocks. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Application of 5388-42-1).

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Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Hemenway, Jeffrey N. et al. published their research in Bioorganic & Medicinal Chemistry Letters in 2007 | CAS: 14204-27-4

2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4) 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. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.COA of Formula: C14H9NO2S

Preparation, characterization and in vivo conversion of new water-soluble sulfenamide prodrugs of carbamazepine was written by Hemenway, Jeffrey N.;Nti-Addae, Kwame;Guarino, Victor R.;Stella, Valentino J.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2007.COA of Formula: C14H9NO2S This article mentions the following:

Improved synthetic methods were reported for the preparation of sulfenamide derivatives I [R = SPh, SCH₂CH(NH₂)CO₂Et, S(CH₂)₂NH₂] of carbamazepine (CBZ) I (R = H) for evaluation as prodrugs. These sulfenamide prodrugs were designed to rapidly release CBZ in vivo by cleavage of the sulfenamide bond by chem. reaction with glutathione and other sulfhydryl compounds Physicochem. characterization and in vivo conversion of the new prodrug I [R = S(CH₂)₂NH₂] of CBZ was evaluated to further establish the proof of concept of the sulfenamide prodrug approach. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4COA of Formula: C14H9NO2S).

Kutuk, Halil et al. published their research in Phosphorus, Sulfur and Silicon and the Related Elements in 2011 | CAS: 14204-27-4

2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4) belongs to indole derivatives. The indole subunit is an almost ubiquitous component of biologically active natural products, and its study has been the focus of research for decades. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Synthetic Route of C14H9NO2S

Microwave-Assisted Synthesis of Disulfides was written by Kutuk, Halil;Turkoz, Nalan. And the article was included in Phosphorus, Sulfur and Silicon and the Related Elements in 2011.Synthetic Route of C14H9NO2S This article mentions the following:

A new microwave-assisted synthesis methodol. for the preparation of substituted disulfide derivatives is presented. 4-Substituted sulfenimides were reacted with 4-substituted thiols under neat (to right doughy consistency) conditions in chloroform, with both microwave heating and conventional methods. The resulting 4-substituted disulfide derivatives were obtained at higher yields and in shorter reaction times with microwave heating. Their chem. was confirmed by ¹H-NMR, ¹³C-NMR, IR, and elemental anal. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4Synthetic Route of C14H9NO2S).

Kaila, Neelu et al. published their research in Journal of Medicinal Chemistry in 2007 | CAS: 150560-58-0

5-Isopropylindoline-2,3-dione (cas: 150560-58-0) 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.Application of 150560-58-0

Synthesis and biological evaluation of quinoline salicylic acids as P-selectin antagonists was written by Kaila, Neelu;Janz, Kristin;DeBernardo, Silvano;Bedard, Patricia W.;Camphausen, Raymond T.;Tam, Steve;Tsao, Desiree H. H.;Keith, James C. Jr.;Nickerson-Nutter, Cheryl;Shilling, Adam;Young-Sciame, Ruth;Wang, Qin. And the article was included in Journal of Medicinal Chemistry in 2007.Application of 150560-58-0 This article mentions the following:

Leukocyte recruitment of sites of inflammation and tissue injury involves leukocyte rolling along the endothelial wall, followed by firm adherence of the leukocyte, and finally transmigration of the leukocyte across cell junctions into the underlying tissue. The initial rolling step is mediated by the interaction of leukocyte glycoproteins containing active moieties such as sialyl Lewis^x (sLe^x) with P-selectin expressed on endothelial cells. Consequently, inhibition of this interaction by means of a small mol. P-selectin antagonist is an attractive strategy for the treatment of inflammatory diseases such as arthritis. High-throughput screening of the Wyeth chem. library identified the quinoline salicylic acid class of compounds as antagonists of P-selectin, with potency in in vitro and cell-based assays far superior to that of sLe^x. Through iterative medicinal chem., it was identified analogs with improved P-selectin activity, decreased inhibition of dihydrooratate dehydrogenase, and acceptable CYP profiles. Lead compound , I, was efficacious in the rat AIA model of rheumatoid arthritis. In the experiment, the researchers used many compounds, for example, 5-Isopropylindoline-2,3-dione (cas: 150560-58-0Application of 150560-58-0).

Yu, Zhengkun et al. published their research in Phosphorus, Sulfur and Silicon and the Related Elements in 1998 | CAS: 14204-27-4

2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Safety of 2-(Phenylthio)isoindoline-1,3-dione

Reductive desulfurization of organosulfur compounds with sodium in liquid ammonia was written by Yu, Zhengkun;Verkade, John G.. And the article was included in Phosphorus, Sulfur and Silicon and the Related Elements in 1998.Safety of 2-(Phenylthio)isoindoline-1,3-dione This article mentions the following:

Greater than 95% sulfur removal was observed when dialkyl mono- or polysulfides were treated with Na in liquid ammonia. Polycyclic aromatic sulfur heterocycles were only moderately desulfurized under these conditions while phenylthio derivatives gave thiophenol as the major product and dithiophenols as the minor products. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4Safety of 2-(Phenylthio)isoindoline-1,3-dione).

Graybill, Todd L. et al. published their research in Journal of the American Chemical Society in 1999 | CAS: 14204-27-4

2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4) 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. 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

Silyl Triflate-Mediated Ring-Closure and Rearrangement in the Synthesis of Potential Bisfuran-Containing Intermediates of Aflatoxin Biosynthesis was written by Graybill, Todd L.;Casillas, Eduard G.;Pal, Kollol;Townsend, Craig A.. And the article was included in Journal of the American Chemical Society in 1999.Related Products of 14204-27-4 This article mentions the following:

The biosynthetic pathway to the potent mycotoxin aflatoxin B₁ (I) is unusually long and complex, proceeding from anthraquinone to xanthone to coumarin nuclear types bearing fused tetrahydro- and bisdihydrofuran rings. A synthetic strategy is described involving two silyl triflate-mediated cyclization and rearrangement processes that have enabled both furofuran oxidation states to be readily achieved and undesired but thermodynamically favorable side reactions to be avoided in the preparation of these ring systems. In the first an o-methoxymethylphenylacetaldehyde is cyclized directly to the five-membered, differentially protected hemiacetal, while in the second this group, appropriately substituted, can be rearranged to a 4-trialkylsilyloxy-2,5-methano-1,3-benzodioxepane. The latter masked dialdehyde is sufficiently stable to strong base, mild acid, and oxidants to allow all needed aryl ring systems to be constructed. Using these methods, total syntheses of (闂?-versicolorin B (II), (闂?-versicolorin A (III), its hemiacetal, and its 6-deoxy derivative, (闂?-6-deoxyversicolorin A, have been achieved, and these are reported herein, as well as preparation of the Me ester of the putative o-carboxybenzophenone biosynthetic intermediate IV. In work described elsewhere, incorporation experiments with ¹³C-labeled forms of these compounds have made possible the complete elucidation of bisfuran biosynthesis characteristic of the first major phase of aflatoxin formation in vivo. 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).

Lu, Lin et al. published their research in Organic Letters in 2019 | CAS: 827-01-0

5-Chloroindole-3-carboxaldehyde (cas: 827-01-0) 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. 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). Safety of 5-Chloroindole-3-carboxaldehyde

Access to Polycyclic Sulfonyl Indolines via Fe(II)-Catalyzed or UV-Driven Formal [2 + 2 + 1] Cyclization Reactions of N-((1H-indol-3-yl)methyl)propiolamides with NaHSO₃ was written by Lu, Lin;Luo, Chenguang;Peng, Hui;Jiang, Huanfeng;Lei, Ming;Yin, Biaolin. And the article was included in Organic Letters in 2019.Safety of 5-Chloroindole-3-carboxaldehyde This article mentions the following:

A variety of structurally novel polycyclic sulfonyl indolines were synthesized via FeCl₂-catalyzed or UV-driven intramol. formal [2 + 2 + 1] dearomatizing cyclization reactions of N-(1H-indol-3-yl)methylpropiolamides with NaHSO₃ in an aqueous medium. The reactions involve the formation of one C-C bond and two C-S bonds in a single step. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Safety of 5-Chloroindole-3-carboxaldehyde).

Matsuoka, Masaru et al. published their research in Shikizai Kyokaishi in 1976 | CAS: 24407-32-7

4,5,6,7-Tetrabromoisoindoline-1,3-dione (cas: 24407-32-7) 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. 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: 24407-32-7

A method to lower the degree of halogenation of polyhalogenated pigments was written by Matsuoka, Masaru;Kitao, Teijiro. And the article was included in Shikizai Kyokaishi in 1976.HPLC of Formula: 24407-32-7 This article mentions the following:

In both pigment systems I and II (Z = p-C6H4, p-C6H4C6H4-p) a benzo substituent on both aromatic rings was intermediate between 4 Cl and 4 Br substituents in its effect on increasing the thermal stability as determined by thermogravimetry. Thus, annellation can be considered as an alternative to halogenation to prepare pigments with greater heat resistance, avoiding the toxicity problems associated with polychloro aromatic compounds In the experiment, the researchers used many compounds, for example, 4,5,6,7-Tetrabromoisoindoline-1,3-dione (cas: 24407-32-7HPLC of Formula: 24407-32-7).

Li, Dingzhong et al. published their research in Catalysis Communications in 2022 | CAS: 4769-96-4

6-Nitro-1H-indole (cas: 4769-96-4) belongs to indole derivatives. The indole subunit is an almost ubiquitous component of biologically active natural products, and its study has been the focus of research for decades.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Synthetic Route of C8H6N2O2

Industrial Cunninghamia lanceolata carbon supported FeO(OH) nanoparticles-catalyzed hydrogenation of nitroarenes was written by Li, Dingzhong;Lu, Hao;Yang, Tianbao;Xing, Chen;Sun, Tulai;Fu, Lihua;Qiu, Renhua. And the article was included in Catalysis Communications in 2022.Synthetic Route of C8H6N2O2 This article mentions the following:

An industrial Cunninghamia lanceolata carbon supported FeO(OH) nanoparticles process for the synthesis of aryl amines with good yields via hydrogenation of nitroarenes was reported. Nine key anti-cancer drug intermediates were successfully achieved with protocol. And Osimertinib intermediate could be smoothly synthesized at a 2.67 kg-scale with >99.5% HPLC purity. This protocol featured cheap carbon source, highly catalytic activity, simple operation, kilogram-scalable and recyclable catalysts (eight times without observable losing activity). In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Synthetic Route of C8H6N2O2).

Alvarez, Estela et al. published their research in Chemistry – A European Journal in 2015 | CAS: 4769-96-4

6-Nitro-1H-indole (cas: 4769-96-4) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Recommanded Product: 6-Nitro-1H-indole

Bronsted Acid-Catalyzed Cascade Reactions Involving 1,2-Indole Migration was written by Alvarez, Estela;Nieto Faza, Olalla;Silva Lopez, Carlos;Fernandez-Rodriguez, Manuel A.;Sanz, Roberto. And the article was included in Chemistry – A European Journal in 2015.Recommanded Product: 6-Nitro-1H-indole This article mentions the following:

A cascade reaction of indoles with propargylic diols involving an unprecedented metal-free 1,2-indole migration onto an alkyne was carried out. DFT calculations support a mechanism consisting of a concerted nucleophilic attack of the indole nucleus with loss of water, followed by the 1,2-migration and subsequent Nazarov cyclization. This Bronsted acid-catalyzed protocol affords indole-functionalized benzofulvene derivatives in high yields. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Recommanded Product: 6-Nitro-1H-indole).