233.22 | - Indole Building Blocks

Baud, Matthias G. J. et al. published their research in Journal of Medicinal Chemistry in 2012 | CAS: 3130-75-4

4-(1,3-Dioxoisoindolin-2-yl)butanoic acid (cas: 3130-75-4) 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.Electric Literature of C12H11NO4

Defining the Mechanism of Action and Enzymatic Selectivity of Psammaplin A against Its Epigenetic Targets was written by Baud, Matthias G. J.;Leiser, Thomas;Haus, Patricia;Samlal, Sharon;Wong, Ai Ching;Wood, Robert J.;Petrucci, Vanessa;Gunaratnam, Mekala;Hughes, Siobhan M.;Buluwela, Lakjaya;Turlais, Fabrice;Neidle, Stephen;Meyer-Almes, Franz-Josef;White, Andrew J. P.;Fuchter, Matthew J.. And the article was included in Journal of Medicinal Chemistry in 2012.Electric Literature of C12H11NO4 This article mentions the following:

Psammaplin A (11c) is a marine metabolite previously reported to be a potent inhibitor of two classes of epigenetic enzymes: histone deacetylases and DNA methyltransferases. The design and synthesis of a focused library based on the psammaplin A core has been carried out to probe the mol. features of this mol. responsible for its activity. By direct in vitro assay of the free thiol generated upon reduction of the dimeric psammaplin scaffold, we have unambiguously demonstrated that 11c functions as a natural prodrug, with the reduced form being highly potent against HDAC1 in vitro (IC₅₀ 0.9 nM). Furthermore, we have shown it to have high isoform selectivity, being 360-fold selective for HDAC1 over HDAC6 and more than 1000-fold less potent against HDAC7 and HDAC8. SAR around our focused library revealed a number of features, most notably the oxime functionality to be important to this selectivity. Many of the compounds show significant cytotoxicity in A549, MCF7, and W138 cells, with the SAR of cytotoxicity correlating to HDAC inhibition. Furthermore, compound treatment causes upregulation of histone acetylation but little effect on tubulin acetylation. Finally, we have found no evidence for 11c functioning as a DNMT inhibitor. In the experiment, the researchers used many compounds, for example, 4-(1,3-Dioxoisoindolin-2-yl)butanoic acid (cas: 3130-75-4Electric Literature of C12H11NO4).

Referemce:
Indole alkaloid derivatives as building blocks of natural products from聽Bacillus thuringiensis聽and聽Bacillus velezensis聽and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Mizrahi, Dana M. et al. published their research in Phosphorus, Sulfur and Silicon and the Related Elements in 2001 | CAS: 3130-75-4

4-(1,3-Dioxoisoindolin-2-yl)butanoic acid (cas: 3130-75-4) 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.Quality Control of 4-(1,3-Dioxoisoindolin-2-yl)butanoic acid

伪-Amino acid derived bisphosphonates. Synthesis and anti-resorptive activity was written by Mizrahi, Dana M.;Waner, Trevor;Segall, Yoffi. And the article was included in Phosphorus, Sulfur and Silicon and the Related Elements in 2001.Quality Control of 4-(1,3-Dioxoisoindolin-2-yl)butanoic acid This article mentions the following:

Eleven new bisphosphonates were prepared from naturally-occurring L-amino acids. The synthesis required special attention to amino and side-chain protections. The novel compounds were tested in TPTX (thyroparathyroidectomized) rats against arotinoid-induced hypercalcemia and were compared to alendronate. Leucine and phenylalanine bisphosphonates showed modest antiresorptive activity, as compared to alendronate. Limited SAR conclusions were drawn. In the experiment, the researchers used many compounds, for example, 4-(1,3-Dioxoisoindolin-2-yl)butanoic acid (cas: 3130-75-4Quality Control of 4-(1,3-Dioxoisoindolin-2-yl)butanoic acid).

Orr, Gary R. et al. published their research in Journal of the American Chemical Society in 1988 | CAS: 3130-75-4

4-(1,3-Dioxoisoindolin-2-yl)butanoic acid (cas: 3130-75-4) 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. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.SDS of cas: 3130-75-4

Synthesis of chirally deuteriated (S-adenosyl-S-methylsulfonio)propylamines and spermidines. Elucidation of the stereochemical course of putrescine aminopropyltransferase (spermidine synthase) was written by Orr, Gary R.;Danz, Deborah W.;Pontoni, Gabriele;Prabhakaran, P. C.;Gould, Steven J.;Coward, James K.. And the article was included in Journal of the American Chemical Society in 1988.SDS of cas: 3130-75-4 This article mentions the following:

The stereochem. course of enzyme-catalyzed aminopropyl transfer was investigated. The stereospecific synthesis of chirally deuteriated (S-adenosyl-S-methylsulfonio)propylamines and several chirally deuteriated spermidine (-)-camphanamide derivatives allowed the elucidation of aminopropyltransferase stereochem. by using ¹H NMR techniques. Putrescine aminopropyltransferase (spermidine synthase) isolated from Escherichia聽coli catalyzed the synthesis of chirally deuteriated spermidines from 1,4-diaminobutane (putrescine) and chirally deuteriated (S-adenosyl-S-methylsulfonio)propylamines. Derivatization of the biosynthetic spermidines to 1,8-bis-(tert-butoxycarbonyl)spermidine (-)-camphanamides and comparison of their ¹H NMR spectra with those of the synthetic standards permits determination of the absolute configuration of the biosynthetic products. The results show that the reaction catalyzed by E. coli spermidine synthase proceeds with inversion of configuration at the methylene carbon undergoing nucleophilic attack by putrescine. These data support a single-displacement mechanism proceeding via a ternary complex of enzyme and both substrates. In the experiment, the researchers used many compounds, for example, 4-(1,3-Dioxoisoindolin-2-yl)butanoic acid (cas: 3130-75-4SDS of cas: 3130-75-4).

4-(1,3-Dioxoisoindolin-2-yl)butanoic acid (cas: 3130-75-4) 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. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.SDS of cas: 3130-75-4

Krysko, Andrei A. et al. published their research in Bioorganic & Medicinal Chemistry in 2013 | CAS: 3130-75-4

4-(1,3-Dioxoisoindolin-2-yl)butanoic acid (cas: 3130-75-4) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Quality Control of 4-(1,3-Dioxoisoindolin-2-yl)butanoic acid

Synthesis, biological evaluation, X-ray molecular structure and molecular docking studies of RGD mimetics containing 6-amino-2,3-dihydroisoindolin-1-one fragment as ligands of integrin 伪_IIb尾₃ was written by Krysko, Andrei A.;Samoylenko, Georgiy V.;Polishchuk, Pavel G.;Fonari, Marina S.;Kravtsov, Victor Ch.;Andronati, Sergei A.;Kabanova, Tatyana A.;Lipkowski, Janusz;Khristova, Tetiana M.;Kuz’min, Victor E.;Kabanov, Vladimir M.;Krysko, Olga L.;Varnek, Alexandre A.. And the article was included in Bioorganic & Medicinal Chemistry in 2013.Quality Control of 4-(1,3-Dioxoisoindolin-2-yl)butanoic acid This article mentions the following:

Acylaminooxoisoindolealkanoic acid RGD mimetics such as tetrahydroisoquinolinecarbonylamino oxoisoindolylpropanoic acid I鈥Cl were prepared as integrin 伪_IIb尾₃ ligands for inhibiting platelet aggregation for potential use as antithrombotic agents. The inhibition of platelet aggregation by the oxoisoindolealkanoic acids was determined, and for some compounds, the inhibition of fluorescein-labeled fibrinogen binding to human platelets (and thus to integrin 伪_IIb尾₃) was also determined; for example, I鈥Cl inhibited platelet aggregation with an IC₅₀ value of 1.1 渭M and inhibited the binding of fluorescein-labeled fibrinogen to platelets with an IC₅₀ value of 6.5 nM. Mol. docking calculations of eight of the prepared compounds bound to integrin 伪_IIb尾₃ were performed, indicating the key interactions present; correlations between docking scores and binding affinities were also found. Of the motifs tried, the use of an N-terminal tetrahydroisoquinolinecarbonyl group and a C-terminal 尾-alanine moiety provided the most effective platelet aggregation inhibitors. The structures for a Me aminooxoisoindolebutanoate, a tetrahydroisoquinolinedicarboxylic acid mono-tert-Bu ester, and solvates, salts, or free bases of five of the oxoisoindolealkanoic acids prepared including I鈥₂O were determined by X-ray crystallog. In the experiment, the researchers used many compounds, for example, 4-(1,3-Dioxoisoindolin-2-yl)butanoic acid (cas: 3130-75-4Quality Control of 4-(1,3-Dioxoisoindolin-2-yl)butanoic acid).

4-(1,3-Dioxoisoindolin-2-yl)butanoic acid (cas: 3130-75-4) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Quality Control of 4-(1,3-Dioxoisoindolin-2-yl)butanoic acid

Terent’ev, Alexander O. et al. published their research in Advanced Synthesis & Catalysis in 2013 | CAS: 1538551-54-0

1,3-Dioxoisoindolin-2-yl butyrate (cas: 1538551-54-0) 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.Application of 1538551-54-0

Oxidative C-O Cross-Coupling of 1,3-Dicarbonyl Compounds and Their Heteroanalogues with N-Substituted Hydroxamic Acids and N-Hydroxyimides was written by Terent’ev, Alexander O.;Krylov, Igor B.;Timofeev, Vladimir P.;Starikova, Zoya A.;Merkulova, Valentina M.;Ilovaisky, Alexey I.;Nikishin, Gennady I.. And the article was included in Advanced Synthesis & Catalysis in 2013.Application of 1538551-54-0 This article mentions the following:

The oxidative C-O cross-coupling of 1,3-dicarbonyl compounds and their heteroanalogs (2-substituted malononitriles and cyanoacetic esters) with N-substituted hydroxamic acids and N-hydroxyimides was realized. The best results were obtained with the use of manganese(III) acetate [Mn(OAc)₃] or the cobalt(II) acetate catalyst [Co(OAc)₂]/potassium permanganate [KMnO₄] system as the oxidant. E.g., in presence of [Co(OAc)₂]/potassium permanganate, cross-coupling of BuCH(COMe)₂ and N-hydroxyphthalimide gave 77% I. The synthesis can be scaled up to gram quantities of coupling products; yields are 30-94%. The reaction proceeds via a radical mechanism through the formation of nitroxyl radicals from N-substituted hydroxamic acids and N-hydroxyimides. In the experiment, the researchers used many compounds, for example, 1,3-Dioxoisoindolin-2-yl butyrate (cas: 1538551-54-0Application of 1538551-54-0).

Serra, A. et al. published their research in Tetrahedron in 1985 | CAS: 3130-75-4

4-(1,3-Dioxoisoindolin-2-yl)butanoic acid (cas: 3130-75-4) 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.SDS of cas: 3130-75-4

New glycidyl ester compounds containing a preformed imide ring – I was written by Serra, A.;Cadiz, V.;Mantecon, A.;Martinez, P. A.. And the article was included in Tetrahedron in 1985.SDS of cas: 3130-75-4 This article mentions the following:

Glycidyl esters I and II [R = glycidyl; X = CH₂, (CH₂)₃, (CH₂)₅, 1,3-phenylene, 1,4-phenylene] were prepared by condensation of I and II (R = H) with a large excess of epichlorohydrin. The structure of glycidyl esters was determined by elementary anal., IR and ¹H and ¹³C NMR spectra. The phys. properties were also defined. In the experiment, the researchers used many compounds, for example, 4-(1,3-Dioxoisoindolin-2-yl)butanoic acid (cas: 3130-75-4SDS of cas: 3130-75-4).

Usifoh, C. O. et al. published their research in Journal of Chemical Society of Nigeria in 2007 | CAS: 3130-75-4

4-(1,3-Dioxoisoindolin-2-yl)butanoic acid (cas: 3130-75-4) 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. 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). Application of 3130-75-4

Ring opening of (1,3-dioxo-1,3-dihydroisoindol-2-yl)amides with amines was written by Usifoh, C. O.;Okunrobo, L. O.;Sanni, S. B.;Oziegbe, F. E.;Ediagbonya, T.. And the article was included in Journal of Chemical Society of Nigeria in 2007.Application of 3130-75-4 This article mentions the following:

The reaction of phthalic anhydride with 尾-alanine and 纬-aminobutyric acid gave the corresponding N-phthaloyl amino acids, which were treated with thionyl chloride to give the acid chlorides I (n = 2, 3). The acid chlorides I were converted to the corresponding N,N-phthaloyl amino acid amides using isopropylamine and benzylamine. Subsequent ring opening of the amides with isopropylamine and benzylamine afforded the corresponding carboxamides II (R = iPr, Bn) in high yield. In the experiment, the researchers used many compounds, for example, 4-(1,3-Dioxoisoindolin-2-yl)butanoic acid (cas: 3130-75-4Application of 3130-75-4).

4-(1,3-Dioxoisoindolin-2-yl)butanoic acid (cas: 3130-75-4) 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. 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). Application of 3130-75-4

Griesbeck, Axel G. et al. published their research in Journal of Organic Chemistry in 2000 | CAS: 3130-75-4

4-(1,3-Dioxoisoindolin-2-yl)butanoic acid (cas: 3130-75-4) 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.Computed Properties of C12H11NO4

Photochemistry of MTM- and MTE-esters of 蠅-phthalimido carboxylic acids: Macrocyclization versus deprotection was written by Griesbeck, Axel G.;Oelgemoller, Michael;Lex, Johann. And the article was included in Journal of Organic Chemistry in 2000.Computed Properties of C12H11NO4 This article mentions the following:

The photolysis of linear methylthiomethyl (MTM) esters of 蠅-phthalimido carboxylic acids, Pht-(CH₂)_n-CO₂CH₂SCH₃ (I; Pht = phthalimido; n = 1, 2, 3, 5, 10), of methylthioethyl (MTE) esters Pht-(CH₂)_n-CO₂CH₂CH₂SCH₃ (II; Pht = phthalimido; n = 1, 3), and of two methyl-substituted esters Pht-CHMeCH₂CO₂CH₂SMe (III) and (S)-Pht-CHMeCO₂CH₂CH₂SMe (IV) resulted in photocyclization to give medium-sized and macrocyclic rings and in photochem. deprotection to give the free carboxylic acids. Photocyclization of I (n = 2, 3) gave the macrocyclic lactones V (n = 2, 3) in excellent yields whereas the substrates I (n = 1, 5, 10) with shorter as well as longer spacer groups gave preferentially deprotected carboxylic acid products. Subsequent photolysis of I (n = 1) gave N-methylphthalimide. Photolysis of the MTE esters II gave the macrocyclic lactones VI and VII. Thus, competition between cyclization and deprotection strongly depended on the chain length of the hydrocarbon linker between phthalimido chromophore and ester group. To examine the influence of the position of the ester group in the linker chain the model substrates III and IV with identical number of atoms separating electron donor and acceptor group were investigated. The more flexible MTE derivative IV cyclized to give a 4:1 diastereoisomeric mixture of 11(S)-cis/trans-indenooxathiaazacyclononanones VIII, whereas photolysis of the more reluctant MTM ester III gave cis-indenooxathiaazacyclononanone IX only after prolonged irradiation Thus, the methylthiomethyl group can function as a photolabile protecting group whereas the methylthioethyl group cannot be removed photochem. The distance dependence of the secondary reaction steps indicates that the primary electron transfer is not necessarily induced starting from close contact geometries. In the experiment, the researchers used many compounds, for example, 4-(1,3-Dioxoisoindolin-2-yl)butanoic acid (cas: 3130-75-4Computed Properties of C12H11NO4).

de Figueiredo, Renata Marcia et al. published their research in Angewandte Chemie, International Edition in 2007 | CAS: 3130-75-4

4-(1,3-Dioxoisoindolin-2-yl)butanoic acid (cas: 3130-75-4) 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.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Name: 4-(1,3-Dioxoisoindolin-2-yl)butanoic acid

Efficient synthesis and resolution of pyrrolizidines was written by de Figueiredo, Renata Marcia;Froehlich, Roland;Christmann, Mathias. And the article was included in Angewandte Chemie, International Edition in 2007.Name: 4-(1,3-Dioxoisoindolin-2-yl)butanoic acid This article mentions the following:

In only two steps the com. available maleimide I is converted into the key pyrrolizidine carboxylic acid unit II of the telomerase inhibitor UCS1025A. A kinetic resolution through an enantioselective oxa-Michael lactonization and trituration of the resulting scalemic mixture allow for a virtually quant. separation of a racemate into the enantiomers. In the experiment, the researchers used many compounds, for example, 4-(1,3-Dioxoisoindolin-2-yl)butanoic acid (cas: 3130-75-4Name: 4-(1,3-Dioxoisoindolin-2-yl)butanoic acid).

4-(1,3-Dioxoisoindolin-2-yl)butanoic acid (cas: 3130-75-4) 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.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Name: 4-(1,3-Dioxoisoindolin-2-yl)butanoic acid

Lu, Fu-Dong et al. published their research in Journal of the American Chemical Society in 2021 | CAS: 1538551-54-0

1,3-Dioxoisoindolin-2-yl butyrate (cas: 1538551-54-0) 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. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.SDS of cas: 1538551-54-0

Enantioselective Radical Carbocyanation of 1,3-Dienes via Photocatalytic Generation of Allylcopper Complexes was written by Lu, Fu-Dong;Lu, Liang-Qiu;He, Gui-Feng;Bai, Jun-Chuan;Xiao, Wen-Jing. And the article was included in Journal of the American Chemical Society in 2021.SDS of cas: 1538551-54-0 This article mentions the following:

1,3-Dienes are readily available feedstocks that are widely used in the laboratory and industry. However, the potential of converting 1,3-dienes into value-added products, especially chiral products, has not yet been fully exploited. By synergetic photoredox/copper catalysis, we achieve the first visible-light-induced, enantioselective carbocyanation of 1,3-dienes by using carboxylic acid derivatives and trimethylsilyl cyanide. Under mild and neutral conditions, a diverse range of chiral allyl cyanides are produced in generally good efficiency and with high enantioselectivity from bench-stable and user-safe chems. Moreover, preliminary results also confirm that this success can be expanded to 1,3-enynes and the four-component carbonylative carbocyanation of 1,3-dienes and 1,3-enynes. In the experiment, the researchers used many compounds, for example, 1,3-Dioxoisoindolin-2-yl butyrate (cas: 1538551-54-0SDS of cas: 1538551-54-0).