cas 48208-26-0, RG108 | Articles data

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Convergent Synthesis of Calcium-Dependent Antibiotic CDA3a and Analogues with Improved Antibacterial Activity via Late-Stage Serine Ligation
A convergent synthesis via the late-stage serine ligation of naturally occurring calcium-dependent antibiotic CDA3a and its analogues has been developed, which allowed us to readily synthesize the analogues with the variation on the lipid tail. Some analogues were found to show 100-500-fold higher antimicrobial activity than the natural compound CDA3a against drug resistant bacteria. This study will enhance our understanding of CDA3a and provide valuable antibacterial lead candidates for further development.
Blasco, Pilar,Chen, Delin,Chen, Sheng,Li, Xuechen,Po, Kathy Hiu Laam
supporting information

(2020/06/29)

Chiral sensors for determining the absolute configurations of α-amino acid derivatives
A simple strategy for configurational assignments of alpha-amino acids has been developed by comparison of the proton NMR chemical shift values of the alpha hydrogens of N-phthaloyl protected alpha-amino acids in the presence of (R)-CSA 1 and (S)-CSA 1, respectively. Highly resolved NMR spectra can be obtained directly on the mixed solution of the chiral solvating agents with N-phthaloyl protected alpha-amino acids in NMR tubes, giving well distinguishable proton signals without interference which dramatically improve the accuracy of assignment and hasten the assigning procedure. The strategy is widely applicable for varied natural and non-natural amino acids.
Chen, Zhongxiang,Fan, Hongjun,Yang, Shiwei,Bian, Guangling,Song, Ling
p. 6933 - 6939
(2018/10/02)

Synthesis and evaluation of analogues of N-phthaloyl-l-tryptophan (RG108) as inhibitors of DNA methyltransferase 1
DNA methyltransferases (DNMT) are promising drug targets in cancer provided that new, more specific, and chemically stable inhibitors are discovered. Among the non-nucleoside DNMT inhibitors, N-phthaloyl-l-tryptophan 1 (RG108) was first identified as inhibitor of DNMT1. Here, 1 analogues were synthesized to understand its interaction with DNMT. The indole, carboxylate, and phthalimide moieties were modified. Homologated and conformationally constrained analogues were prepared. The latter were synthesized from prolinohomotryptophan derivatives through a methodology based amino-zinc-ene-enolate cyclization. All compounds were tested for their ability to inhibit DNMT1 in vitro. Among them, constrained compounds 16-18 and NPys derivatives 10-11 were found to be at least 10-fold more potent than the reference compound. The cytotoxicity on the tumor DU145 cell line of the most potent inhibitors was correlated to their inhibitory potency. Finally, docking studies were conducted in order to understand their binding mode. This study provides insights for the design of the next-generation of DNMT inhibitors.
Asgatay, Saa?dia,Champion, Christine,Marloie, Ga?l,Drujon, Thierry,Senamaud-Beaufort, Catherine,Ceccaldi, Alexandre,Erdmann, Alexandre,Rajavelu, Arumugam,Schambel, Philippe,Jeltsch, Albert,Lequin, Olivier,Karoyan, Philippe,Arimondo, Paola B.,Guianvarc'H, Dominique
p. 421 - 434
(2014/02/14)

Phthaloyl amino acids as anti-inflammatory and immunomodulatory prototypes
A series of phthalimide analogs were synthesized by derivatization of phthalic anhydride, a highly toxic substance, using a "one pot" condensation reaction to α-amino acids. All phthaloyl amino acid derivatives presented anti-oral inflammatory activity, but compounds 2e and 2g were found to possess the best activities comparable to thalidomide.Most of the compounds effectively suppressed nitric oxide production inmurine cells stimulatedwith lipopolysaccharide. N-phthaloyl amino acids did not exhibit any significant cytotoxicity in vitro when tested against tumor cells as well as a spleen cell culture of BALB/c mice. Compounds 2a, 2g, and 2h were able to inhibit TNF-α and IL-1β production by macrophages. At the same concentration, thalidomide did not exhibit significant inhibitory activity. Springer Science+Business Media 2013.
Leite, Ana Cristina Lima,Barbosa, Fabio Fernandes,Cardoso, Marcos Verissimo De Oliveira,Moreira, Diogo R. M.,Coelho, Lucas Cunha D.,Da Silva, Elany Barbosa,Filho, Gevanio Bezerra De Oliveira,De Souza, Valdenia Maria Oliveira,Pereira, Valeria Rego A.,Reis, Luiza De C.,Ferreira, Paulo Michel Pinheiro,Pessoa, Claudia,Wanderley, Almir Goncalves,Mota, Fernanda Virginia B.,Da Silva, Teresinha G.
p. 1701 - 1708
(2014/05/06)

Stereoselective synthesis of brevianamide e
The hydroxypyrroloindolenine (Hpi) motif forms the fundamental core of the pentacyclic natural product, brevianamide E, the concise stereoselective synthesis of which, via oxidative cyclization, is described.
Zhao, Liang,May, Jonathan P.,Huang, Jack,Perrin, David M.
supporting information; experimental part
p. 90 - 93
(2012/02/15)

Photoinduced electron-transfer chemistry of the bielectrophoric N-phthaloyl derivatives of the amino acids tyrosine: Histidine and tryptophan
The photochemistry of phthalimide derivatives of the electron-rich amino acids tyrosine, histidine and tryptophan 8-10 was studied with respect to photoinduced electron-transfer (PET)induced decarboxylation and Norrish II bond cleavage. Whereas exclusive photodecarboxylation of the tyrosine substrate 8 was observed, the histidine compound 9 resulted in a mixture of histamine and preferential Norrish cleavage. The tryptophan derivative 10 is photochemically inert and shows preferential decarboxylation only when induced by intermolecular PET.
Griesbeck, Axel G.,Neudoerfl, Joerg,Kiff, Alan De
experimental part
p. 518 - 524
(2011/06/28)

Synthesis and characterization of bioactive molecules grafted on poly(e{open}-caprolactone) by " click" chemistry
A facile and efficient strategy to graft bioactive molecules (nicotinic acid, p-aminobenzoic acid, and phthaloyltryptophan) onto poly(e{open}-caprolactone) (P(e{open}CL)) was achieved by copper-catalyzed Huisgen's 1,3-dipolar cycloaddition known as click reaction. P(αCle{open}CL), with 10, 20, and 30% of α-chloro-e{open}-caprolactone (αCle{open}CL) units were copolymerized by ring opening polymerization using e{open}CL and αCle{open}CL as starting materials in the presence of 1,4-butanediol and Sn(Oct)2. Subsequently, the chloride pendent was converted to azide followed by cycloaddition with terminal alkyne derivatives of the aforementioned bioactive molecules. The complete addition was accomplished at all ratios. The characteristic molecular features of these copolymers were evaluated by FTIR, NMR, and GPC. Thermal analysis data indicated that the grafted compounds led to polymorphic alteration and different pattern of thermal degradation depending on the molecular structure and the size of the grafted compounds. They are the basis for further development of grafted copolymer as drug delivery carriers.
Suksiriworapong, Jiraphong,Sripha, Kittisak,Junyaprasert, Varaporn Buraphacheep
experimental part
p. 2286 - 2295
(2011/10/05)

PHTHALAMIDES, SUCCINIMIDES AND RELATED COMPOUNDS AND THEIR USE AS PHARMACEUTICALS
The present invention relates to certain phthalamides, succinimides and related compounds and their use as pharmaceuticals. In particular, the present invention relates to these compounds, pharmaceutical compositions comprising these compounds, and use of these compounds, for example, to inhibit DNA methylation in cells, particularly tumour cells.
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Page/Page column 48; 53

(2008/06/13)

Cyclomaltooligosaccharide-assisted spectroscopic discrimination of phthalimido-derived amino acids through the formation of molecular aggregates
Spectroscopic evidence was used to demonstrate the formation of molecular associates in an aqueous solution of phthalimido tryptophan. These molecular associates are loosely formed through π-π aromatic stacking, properties that are not sufficient to cause NMR spectroscopic enantiomeric discrimination. A cyclomaltooligosaccharide with a larger cavity, such as cyclomaltooctaose (γ-cyclodextrin), is capable of forming a ternary complex with these molecular associates and enhances π-π aromatic stacking interactions, resulting in NMR enantiomeric discrimination. Electrospray-ionization mass spectroscopy (ESIMS) and NOESY two-dimensional NMR spectroscopic methods were used to study these complexes. Association constants and thermodynamic data for these cyclomaltooligosaccharide complexes were also estimated.
Jursic, Branko S.,Patel, Paresh K.
p. 2858 - 2866
(2007/10/03)

Inhibitors of DNA methylation in tumor cells
The present invention relates to compounds according to the general formula wherein the dotted lines denote a single bond which is optionally present, with 2 dotted lines denoting a double bond; and wherein the symbols in particular have the following meanings: R1 and R2 are independently from each other selected from the group consisting of: H; OH; (=O); halogens; pseudohalogens; NH2; S(O)mR5; SO2NH2; C(O)R8; C(O)OR9; CONH2; C1-C2-alkyl substituted by NH2, OH, S(O)mR5, SO2NH2, C(O)R8, C(O)OR9, CONH2; C1-C2-alkoxy substituted by NH2, OH, S(O)mR5, SO2NH2, C(O)R8, C(O)OR9, CONH2; Ar denotes an unsubstituted mononuclear aryl group having 6 or 7 members, which aryl group is annulated to the neighbouring 5-membered cycle, and which may carry 1, 2 or 3 heteroatoms from the group N, O and S in its cycle; Y, Z denote independently from each other a nitrogen atom or a methylene group; X is a nitrogen atom or a methylene group; A is selected from the group consisting of: H; halogens and pseudohalogens; OH; =N(OH); NR12R13; OSO3-; S(O)mR14; SO2NR15R16; C(O)R17; C(O)OR18; CONR19R20; C(S)R21, C(S)OR22; unsubstituted and at least monosubstituted C1-C6-alkyl which can carry in its chain one or more non-adjacent heteroatoms from the group nitrogen and oxygen, and which, if substituted, carry at least one substituent which is preferably selected from the group consisting of: halogens, pseudohalogens, OH, NR12R13, OSO3-, S(O)mR14, SO2NR15R16, C(O)R17, C(O)OR18, CONR19R20, C(S)R21, C(S)OR22, and substituted and non-substituted aryl and substituted and non-substituted heteroaryl which, if substituted, carry at least one substituent from the group consisting of C1-C3-alkyl, C1-C3-alkoxy, halogens, pseudohalogens, and CF3. These compounds lend themselves for the manufacture of drugs. They are useful in the inhibition of DNA methylation, the inhibition of DNA methyltransferases, and may therefore be useful for the manufacture of pharmaceuticals for the treatment of developmental disorders such as Prader-Willi-Syndrome, Angelman-Syndrome (Happy Puppet Syndrome), Beckwith-Wiedemann-Syndrome, and proliferative diseases, such as coronary restenosis and neoplastic diseases, particularly colon carcinoma, familiary adenomatous polyposis carcinoma and hereditary non-polyposis colorectal cancer, prostate carcinoma, melanoma, non-Hodgkin lymphoma, acute lymphatic leukemia (ALL), chronic lymphatic leukemia (CLL), acute myeolid leukemia (AML), chronic myeloid leukemia (CML), or hepatocellular carcinoma. These compounds may also be used for other applications including the induction of cellular differentiation, diagnosis, and the use in screening assays.
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Page/Page column 14

(2008/06/13)

Methyl 2-((succinimidooxy)carbonyl)benzoate (MSB): a new, efficient reagent for N-phthaloylation of amino acid and peptide derivatives.
A new, efficient, and readily available reagent, methyl 2-((succinimidooxy)carbonyl)benzoate (MSB), for N-phthaloylation of amino acids and amino acid derivatives is described. The phthaloylation procedure is simple and racemization-free and gives excellent results with alpha-amino acids, alpha-amino alcohols, dipeptides, alpha-amino carboxamides, and alpha-amino esters.
Casimir, J Richard,Guichard, Gilles,Briand, Jean-Paul
p. 3764 - 3768
(2007/10/03)

Novel α-amino acid-based hydroxamic acid ligands for vanadium-catalyzed asymmetric epoxidation of allylic alcohols [2]
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Hoshino,Yamamoto
p. 10452 - 10453
(2007/10/03)