Tag: M.W=350-400

Schwickert, Marvin published the artcileDiscovery of Inhibitors of DNA Methyltransferase 2, an Epitranscriptomic Modulator and Potential Target for Cancer Treatment, Application of (S)-tert-Butyl 2-((tert-butoxycarbonyl)amino)-4-iodobutanoate, the publication is Journal of Medicinal Chemistry (2022), 65(14), 9750-9788, database is CAplus and MEDLINE.

Selective manipulation of the epitranscriptome could be beneficial for the treatment of cancer and also broaden the understanding of epigenetic inheritance. Inhibitors of the tRNA methyltransferase DNMT2, the enzyme catalyzing the S-adenosylmethionine-dependent methylation of cytidine 38 to 5-methylcytidine, were designed, synthesized, and analyzed for their enzyme-binding and -inhibiting properties. For rapid screening of potential DNMT2 binders, a microscale thermophoresis assay was established. Besides the natural inhibitors S-adenosyl-L-homocysteine (SAH) and sinefungin (SFG), we identified new synthetic inhibitors based on the structure of N-adenosyl-2,4-diaminobutyric acid (Dab). Structure-activity relationship studies revealed the amino acid side chain and a Y-shaped substitution pattern at the 4-position of Dab as crucial for DNMT2 inhibition. The most potent inhibitors are alkyne-substituted derivatives, exhibiting similar binding and inhibitory potencies as the natural compounds SAH and SFG. CaCo-2 assays revealed that poor membrane permeabilities of the acids and rapid hydrolysis of an ethylester prodrug might be the reasons for the insufficient activity in cellulo.

Journal of Medicinal Chemistry published new progress about 161370-66-7. 161370-66-7 belongs to iodides-buliding-blocks, auxiliary class Chiral,Iodide,Amine,Aliphatic hydrocarbon chain,Ester,Amide, name is (S)-tert-Butyl 2-((tert-butoxycarbonyl)amino)-4-iodobutanoate, and the molecular formula is C6H3ClFNO2, Application of (S)-tert-Butyl 2-((tert-butoxycarbonyl)amino)-4-iodobutanoate.

Referemce:
https://en.wikipedia.org/wiki/Iodide,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Ciapetti, Paola published the artcile2-Amino-4-bromobutanoic acid. A versatile reagent for the synthesis of nonnatural amino acids, Synthetic Route of 161370-66-7, the publication is Molecules Online [Electronic Publication] (1998), 2(2), 86-93, database is CAplus.

(2S)- and (2R)-2-Amino-4-bromobutanoic acid derivatives were prepared starting from Boc-L– and –D-Glu-OCMe₃. The double tert-Bu protection was necessary to prevent a partial racemization during the Barton radical decarboxylation used to transform the γ-carboxylic group into a bromide. This bromide reacted with different nitrogen, oxygen and sulfur nucleophiles to give nonnatural amino acids, e.g. I [R = piperidino, pyrrolidino, morpholino, pyrazolo, NH(CH₂)₁₅Me, NHC₆H₃(OMe)₂-2,5, OPh, iodo], characterized by basic or heterocyclic side chains. The title compound was also used to prepare conformationally constrained peptidomimetic II.

Molecules Online [Electronic Publication] published new progress about 161370-66-7. 161370-66-7 belongs to iodides-buliding-blocks, auxiliary class Chiral,Iodide,Amine,Aliphatic hydrocarbon chain,Ester,Amide, name is (S)-tert-Butyl 2-((tert-butoxycarbonyl)amino)-4-iodobutanoate, and the molecular formula is C13H24INO4, Synthetic Route of 161370-66-7.

Referemce:
https://en.wikipedia.org/wiki/Iodide,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Wisniewski, Kazimierz published the artcileOn the mechanism of degradation of oxytocin and its analogues in aqueous solution, Application of (S)-tert-Butyl 2-((tert-butoxycarbonyl)amino)-4-iodobutanoate, the publication is Biopolymers (2013), 100(4), 408-421, database is CAplus and MEDLINE.

Oxytocin (OT) is a cyclic nonapeptide containing one internal disulfide bond between its Cys¹ and Cys⁶ residues. Although OT is one of the most commonly used peptidic drugs, the mechanism of its degradation in aqueous solution and the identity of its degradants have not been fully elucidated. To investigate the pathways and products of OT degradation in slightly acidic to neutral solutions, we prepared the peptides: OT, [D-Cys¹]OT, a series of N-alkylated OT analogs, [[¹³C₃,¹⁵N]Cys¹]OT, and OT where each sulfur atom was systematically replaced by either methylene, ³⁴S, or Se. The peptides were incubated at 40°C and the degradation products studied by HPLC, LCMS, and ¹³C-NMR. Our findings suggest that the degradation begins with β-elimination of the disulfide linkage to form a putative intermediate linear peptide containing an S-thiocysteine (a persulfide) in position 6 and a dehydroalanine in position 1. This intermediate persulfide appears to donate a sulfur atom to an intact OT mol. to form OT trisulfide and higher monomeric polysulfides, while the dehydroalanine residue is hydrolyzed with loss of the N-terminal amino group to yield a linear N-pyruvoylated octapeptide containing a reduced Cys⁶. Based on the MS and ¹³C-NMR data of the products from degradation of [[¹³C₃,¹⁵N]Cys¹]OT, we postulate that the ultimate degradation products of OT are dimers composed of two pyruvoylated octapeptides held together by one disulfide bridge between the two Cys⁶ residues and by one more, non-reducible, linkage resulting from an aldol-type condensation between the two N-terminal pyruvoyl groups.

Biopolymers published new progress about 161370-66-7. 161370-66-7 belongs to iodides-buliding-blocks, auxiliary class Chiral,Iodide,Amine,Aliphatic hydrocarbon chain,Ester,Amide, name is (S)-tert-Butyl 2-((tert-butoxycarbonyl)amino)-4-iodobutanoate, and the molecular formula is C9H22OSi, Application of (S)-tert-Butyl 2-((tert-butoxycarbonyl)amino)-4-iodobutanoate.

Referemce:
https://en.wikipedia.org/wiki/Iodide,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Longobardo, Luigi published the artcileNovel thiol- and thioether-containing amino acids: cystathionine and homocysteine families, Synthetic Route of 161370-66-7, the publication is Amino Acids (2013), 44(2), 443-448, database is CAplus and MEDLINE.

Natural L-homocysteine and L,L-cystathionine, along with a series of unnatural analogs, have been prepared from L-aspartic and L-glutamic acids. Manipulation of the protected derivatives provided ω-iodoamino acids, which were used in thioalkylation reactions of sulfur nucleophiles, such as the ester of L-cysteine and potassium thioacetate.

Amino Acids published new progress about 161370-66-7. 161370-66-7 belongs to iodides-buliding-blocks, auxiliary class Chiral,Iodide,Amine,Aliphatic hydrocarbon chain,Ester,Amide, name is (S)-tert-Butyl 2-((tert-butoxycarbonyl)amino)-4-iodobutanoate, and the molecular formula is C13H24INO4, Synthetic Route of 161370-66-7.

Referemce:
https://en.wikipedia.org/wiki/Iodide,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Nino, Patricia published the artcileEfficient three-component synthesis of diversely substituted tetrahydro-1H-cyclopenta[c]quinolines, Synthetic Route of 364-12-5, the publication is Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry (2016), 55B(7), 854-881, database is CAplus.

The synthesis of highly functionalized substituted tetrahydro-1H-cyclopenta[c]quinoline and its reduced derivatives hexahydro-1H-cyclopenta[c]quinolines via Povarov reaction in high diastereoselectivity and high to moderate yields is described. In addition, the relative stereochem. of the α-substituent to the tetrahydroquinoline nitrogen, as well as the regioselectivity of reaction, is shown to depend upon subtle substituent effects on the aldehyde and aniline precursors. In most cases, a preference for the formation of endo diastereomeric adducts is observed but for reactions with ortho-substituted aldehydes, the formation of exo adducts is also observed The exo-diastereoselectivity is found to be higher when the bulky size of this ortho group increases. Preparation of ortho and diortho-substituted aromatic aldehyde precursors of the Povarov reaction is also reported.

Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry published new progress about 364-12-5. 364-12-5 belongs to iodides-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Bromide,Iodide,Benzene, name is 5-Bromo-2-iodobenzotrifluoride, and the molecular formula is C7H3BrF3I, Synthetic Route of 364-12-5.

Referemce:
https://en.wikipedia.org/wiki/Iodide,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Alami, Anouar published the artcileSynthesis and characterization of some linear sulfur-containing analogues of quisqualic acid, COA of Formula: C13H24INO4, the publication is Journal Marocain de Chimie Heterocyclique (2016), 15(1), 57-61, database is CAplus.

The compounds such as 3-(1-(benzyloxy)-3-(ethoxycarbonyl)thioureido)-2-(tert-butoxycarbonyl) propanoic acid and 2-amino-4-(1-(benzyloxy)-3-(ethoxycarbonyl)thioureido)butanoic acid have been synthesized resp. via an opening reaction of α-(N-Boc) amino- β-lactone and a reaction of substitution carried out on γ-iodohomoalanine. The structures of the synthesized compounds were established by 1H-NMR, MS data and elemental anal.

Journal Marocain de Chimie Heterocyclique published new progress about 161370-66-7. 161370-66-7 belongs to iodides-buliding-blocks, auxiliary class Chiral,Iodide,Amine,Aliphatic hydrocarbon chain,Ester,Amide, name is (S)-tert-Butyl 2-((tert-butoxycarbonyl)amino)-4-iodobutanoate, and the molecular formula is C13H24INO4, COA of Formula: C13H24INO4.

Referemce:
https://en.wikipedia.org/wiki/Iodide,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com