Day: February 10, 2023

Applied Enantioselective Aminocatalysis: α-Heteroatom Functionalization Reactions on the Carbapenem (β-Lactam Antibiotic) Core was written by Cele, Zamani E. D.;Arvidsson, Per I.;Kruger, Hendrik G.;Govender, Thavendran;Naicker, Tricia. And the article was included in European Journal of Organic Chemistry in 2015.Product Details of 14204-27-4 This article mentions the following:

The carbapenem (β-lactam antibiotic) scaffold serves as a useful nucleophile in organocatalytic diarylprolinol trimethylsilyl ether mediated α-heterofunctionalization reactions leading to the formation of diverse products that bear multiple stereocenters in high diastereoselectivity and moderate to good yields. Under optimized conditions the synthesis of the target compounds was achieved using (2S)-2-[diphenyl[(trimethylsilyl)oxy]methyl]pyrrolidine (chiral prolinol-silyl ether) as a catalyst. Starting materials included (5R,6S)-6-[(1R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid (4-nitrophenyl)methyl ester, 1,2-diazenedicarboxylic acid, 1,2-bis(1,1-dimethylethyl) ester, N-(hydroxy)carbamic acid ester, (nitros)benzene,2-(phenylthio)-1H-isoindole-1,3(2H)-dione, 2-(phenylseleno)-1H-i-Isoindole-1,3(2H)-dione. 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).

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

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

Formation of the secondary abscission zone induced by the interaction of methyl jasmonate and auxin in Bryophyllum calycinum: relevance to auxin status and histology was written by Marasek-Ciolakowska, Agnieszka;Saniewski, Marian;Dziurka, Michal;Kowalska, Urszula;Goraj-Koniarska, Justyna;Ueda, Junichi;Miyamoto, Kensuke. And the article was included in International Journal of Molecular Sciences in 2020.Quality Control of 2-(5-Chloro-1H-indol-3-yl)acetic acid This article mentions the following:

The interaction of Me jasmonate (JA-Me) and indole-3-acetic acid (IAA) to induce the formation of the secondary abscission zone in the middle of internode segments of Bryophyllum calycinum was investigated in relation to auxin status and histol. When IAA at 0.1% (weight/weight, in lanolin) was applied to the segments, the formation of the secondary abscission zone at a few mm above the treatment in the apical direction was observed On the contrary, IAA at 0.5% (weight/weight, in lanolin) did not induce the formation of the secondary abscission zone. JA-Me at 0.5% (weight/weight, in lanolin) applied to the middle of internode segments kept in the normal (natural) or inverted positions also induced the formation of the secondary abscission zone below and above parts of the treatment. Comprehensive analyses of plant hormones revealed that the balance of the endogenous levels of IAA in both sides adjacent to the abscission zone was significantly disturbed when the secondary abscission formation was induced by the application of IAA. These results strongly suggest that an auxin gradient is important in the formation of the secondary abscission zone in the internode segments of B. calycinum, and IAA gradient results from polar IAA transport from the application site. Further possible mechanisms of the formation of the secondary abscission zone in the internode segments of B. calycinum are also discussed in the interaction of JA-Me and IAA. In the experiment, the researchers used many compounds, for example, 2-(5-Chloro-1H-indol-3-yl)acetic acid (cas: 1912-45-4Quality Control of 2-(5-Chloro-1H-indol-3-yl)acetic acid).

2-(5-Chloro-1H-indol-3-yl)acetic acid (cas: 1912-45-4) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana. 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). Quality Control of 2-(5-Chloro-1H-indol-3-yl)acetic acid

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

Carbonylation of doubly lithiated N’-aryl-N,N-dimethylureas: A novel approach to isatins via intramolecular trapping of acyllithiums was written by Smith, Keith;El-Hiti, Gamal A.;Hawes, Anthony C.. And the article was included in Synthesis in 2003.Name: 5-Isopropylindoline-2,3-dione This article mentions the following:

Lithiation of N’-(2-bromoaryl)-N,N-dimethylureas with methyllithium and tert-butyllithium under nitrogen in anhydrous THF at 0 °C gave doubly lithiated arylurea derivatives, which react with carbon monoxide at 0 °C to give isatins in good yields. The scope of the reaction has been demonstrated by application to the synthesis of isatin itself and four substituted isatins bearing alkyl, chloro or fluoro groups. Double lithiation and quenching with ammonium chloride of N‘-(2-bromophenyl)-N,N-dimethylurea gave N‘-(2-bromophenyl)-N,N-dimethylurea. Lithiation of N‘-(2-bromophenyl)-N,N-dimethylurea with methyllithium was followed by addition of (1,1-dimethylethyl)lithium, effecting an bromine-lithium exchange. Sequential carbonylation with carbon monoxide and quenching gave 1H-indole-2,3-dione (isatin). In the experiment, the researchers used many compounds, for example, 5-Isopropylindoline-2,3-dione (cas: 150560-58-0Name: 5-Isopropylindoline-2,3-dione).

5-Isopropylindoline-2,3-dione (cas: 150560-58-0) 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 was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Name: 5-Isopropylindoline-2,3-dione

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

Synthesis and application of P,olefin type axially chiral ligands with sec-alkyl groups was written by Mino, Takashi;Yamaguchi, Daiki;Masuda, Chihiro;Youda, Junpei;Ebisawa, Toshibumi;Yoshida, Yasushi;Sakamoto, Masami. And the article was included in Organic & Biomolecular Chemistry in 2019.Quality Control of 6-Nitro-1H-indole This article mentions the following:

We synthesized N-trans-cinnamyl-N-cyclohexylaniline type aminophosphine 2 and a series of N-2-adamantyl-N-trans-cinnamylaniline type aminophosphines 3. Although aminophosphine 2 failed to find the existence of axial chirality, aminophosphines 3, which exist in the axial chirality in a C(aryl)-N(amine) bond by chiral HPLC anal. as 1-adamantyl type chiral ligands 1. Enantiomeric isomers of 3b, 3c, and 3d were obtained in an enantiomerically pure form. We also identified the palladium-catalyzed asym. allylic substitution of 1,3-diphenyl-2-propenyl acetate with indoles using aminophosphines 3b–d as effective chiral ligands in high enantioselectivities (up to 96% ee). In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Quality Control of 6-Nitro-1H-indole).

6-Nitro-1H-indole (cas: 4769-96-4) 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.Quality Control of 6-Nitro-1H-indole

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

Improved synthesis of 3-spiro indolines in dry media under microwave irradiation was written by Dandia, Anshu;Sachdeva, Harshita;Singh, Ruby. And the article was included in Synthetic Communications in 2001.Synthetic Route of C8H4N2O4 This article mentions the following:

The spiro[indole-dipyrrolopyridines] I (X = NH; R = H, Me; R¹, R² = F, H; H, NO₂; Me, Me; NO₂, H; H, NO₂) were prepared in an efficient, one-pot synthesis using microwave irradiation by reaction of spiro[indole-dipyrrolopyrans] I (X = O) with ammonium acetate in the presence of acetic acid. I (X = O) were prepared in situ by microwave induced reaction of indole-2,3-diones and 2-pyrrolidones in a 1:2 molar ratio. Comparative studies were made between microwave irradiation of reactants in the absence of any solvent and catalyzed reactions in the presence of o-dichlorobenzene and classical heating. In the experiment, the researchers used many compounds, for example, 7-Nitroindoline-2,3-dione (cas: 112656-95-8Synthetic Route of C8H4N2O4).

7-Nitroindoline-2,3-dione (cas: 112656-95-8) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana. 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). Synthetic Route of C8H4N2O4

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

Synthesis and screening of 2-hydroxy-N-(2,41-dioxospiro [indoline-3,21-thiazolidin]-31-yl) benzamides for antiinflammatory activity was written by Devi, N. Saritha;Sarangapani, Manda. And the article was included in International Journal of Pharmacy and Biological Sciences in 2018.SDS of cas: 112656-95-8 This article mentions the following:

A novel synthesis of 2-hydroxy-N-(2,4′-dioxospiro[indoline-3,2′-thiazolidin]-3′-yl)benzamide derivatives I [R = H, 5-F, 5,6-dichloro, etc.] was synthesized by cyclization of isatin hydrazones with thioglycollic acid. The synthesized compounds I were characterized by spectral data (IR, ¹H-NMR, MASS) and evaluated for in-vitro, in-vivo anti-inflammatory activity. The test compounds I exhibited significant potency to inhibit COX-2 enzyme values between 46.23 ± 0.38 to 73.24 ± 0.35, Among the tested compounds compounds I [R = 5,6-dichloro, 5-F, 5-Cl] were considered to possess more potent anti-inflammatory activity when compared to standard drug indomethacin. By in-vitro anti-inflammatory activity the compounds I [R = 5,6-dichloro, 5-F, 5-Cl, 5-Br] were considered to possess more potent anti-inflammatory activity when compared to standard drug indomethacin. In the experiment, the researchers used many compounds, for example, 7-Nitroindoline-2,3-dione (cas: 112656-95-8SDS of cas: 112656-95-8).

7-Nitroindoline-2,3-dione (cas: 112656-95-8) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.SDS of cas: 112656-95-8

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

Efficient preparation of N-phenylsulfenyl ketimines from oximes or nitro compounds without racemization of α-stereocenters was written by Bures, Jordi;Isart, Carles;Vilarrasa, Jaume. And the article was included in Organic Letters in 2007.Category: indole-building-block This article mentions the following:

As N-sulfenyl imines, e.g., I, could be readily transformed to their N-sulfinyl imines, N-sulfonyl imines , and N-sulfonyl oxaziridines, the very mild procedure developed to convert ketoximes and secondary nitro derivatives to N-arenesulfenyl ketimines constituted an efficient route to all these series of compounds The configuration of the α-stereocenters was retained. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4Category: indole-building-block).

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. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.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

Probing the Subpockets of Factor Xa Reveals Two Binding Modes for Inhibitors Based on a 2-Carboxyindole Scaffold: A Study Combining Structure-Activity Relationship and X-ray Crystallography was written by Nazare, Marc;Will, David W.;Matter, Hans;Schreuder, Herman;Ritter, Kurt;Urmann, Matthias;Essrich, Melanie;Bauer, Armin;Wagner, Michael;Czech, Joerg;Lorenz, Martin;Laux, Volker;Wehner, Volkmar. And the article was included in Journal of Medicinal Chemistry in 2005.Name: Methyl 5-bromo-1H-indole-2-carboxylate This article mentions the following:

Structure-activity relationships within a series of highly potent 2-carboxyindole-based factor Xa inhibitors incorporating a neutral P1 ligand are described with particular emphasis on the structural requirements for addressing subpockets of the factor Xa enzyme. Interactions with the subpockets were probed by systematic substitution of the 2-carboxyindole scaffold, in combination with privileged P1 and P4 substituents. Combining the most favorable substituents at the indole nucleus led to the discovery of a remarkably potent factor Xa inhibitor displaying a K_i value of 0.07 nM. X-ray crystallog. of inhibitors bound to factor Xa revealed substituent-dependent switching of the inhibitor binding mode and provided a rationale for the SAR obtained. These results underscore the key role played by the P1 ligand not only in determining the binding affinity of the inhibitor by direct interaction but also in modifying the binding mode of the whole scaffold, resulting in a nonlinear SAR. In the experiment, the researchers used many compounds, for example, Methyl 5-bromo-1H-indole-2-carboxylate (cas: 210345-56-5Name: Methyl 5-bromo-1H-indole-2-carboxylate).

Methyl 5-bromo-1H-indole-2-carboxylate (cas: 210345-56-5) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Name: Methyl 5-bromo-1H-indole-2-carboxylate

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

Design, synthesis, and biological evaluation of N-(3-cyano-1H-indol-5/6-yl)-6-oxo-1,6-dihydropyrimidine-4-carboxamides and 5-(6-oxo-1,6-dihydropyrimidin-2-yl)-1H-indole-3-carbonitriles as novel xanthine oxidase inhibitors was written by Zhang, Bing;Duan, Yulin;Yang, Yuwei;Mao, Qing;Lin, Fengwei;Gao, Jun;Dai, Xiwen;Zhang, Peng;Li, Qiuhua;Li, Jinxin;Dai, Ronghua;Wang, Shaojie. And the article was included in European Journal of Medicinal Chemistry in 2022.Formula: C8H6N2O2 This article mentions the following:

Xanthine oxidase (XO) has been an important target for the treatment of hyperuricemia and gout. The anal. of potential interactions of pyrimidinone and 3-cyano indole pharmacophores present in the corresponding reported XO inhibitors with parts of the XO active pocket indicated that they both can be used as effective fragments for the fragment-based design of nonpurine XO inhibitors. In this paper, we adopted the fragment-based drug design strategy to link the two fragments with an amide bond to design the type 1 compounds 13a-13w,14c, 14d, 14f, 14g, 14j, 14k, and 15g. Compound 13g displayed an evident XO inhibitory potency (IC₅₀ = 0.16 μM), which was 52.3-fold higher than that of allopurinol (IC₅₀ = 8.37 μM). For comparison, type 2 compounds 5-(6-oxo-1,6-dihydropyrimidin-2-yl)-1H-indole-3-carbonitriles (25c-25g) were also designed by linking the two fragments with a single bond directly. The results showed that compound 25c from the latter series displayed the best inhibitory potency (IC₅₀ = 0.085 μM), and it was 98.5-fold stronger than that of allopurinol (IC₅₀ = 8.37 μM). These results suggested that amide and single bonds were applicable for linking the two fragments together to obtain potent nonpurine XO inhibitors. The structure-activity relationship results revealed that hydrophobic groups at N-atom of the indole moiety were indispensable for the improvement of the inhibitory potency in vitro against XO. In addition, enzyme kinetics studies suggested that compounds 13g and 25c, as the most promising XO inhibitors for the two types of target compounds, acted as mixed-type inhibitors for XO. Moreover, mol. modeling studies suggested that the pyrimidinone and indole moieties of the target compounds could interact well with key amino acid residues in the active pocket of XO. Furthermore, in vivo hypouricemic effect demonstrated that compounds 13g and 25c could effectively reduce serum uric acid levels at an oral dose of 10 mg/kg. Therefore, compounds 13g and 25c could be potential and efficacious agents for the treatment of hyperuricemia and gout. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Formula: C8H6N2O2).

6-Nitro-1H-indole (cas: 4769-96-4) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Formula: C8H6N2O2

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