Category: 3130-75-4

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).

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

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

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).

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

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

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

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

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

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