Category: 617-55-0

Levy, Daniel E.; Lapierre, France; Liang, Weisheng; Ye, Wenqing; Lange, Christopher W.; Li, Xiaoyuan; Grobelny, Damian; Casabonne, Marie; Tyrrell, David; Holme, Kevin; Nadzan, Alex; Galardy, Richard E. published the artcile< Matrix Metalloproteinase Inhibitors: A Structure Activity Study>, Application of C6H10O5, the main research area is matrix metalloproteinase inhibitor preparation structure activity; stromelysin inhibitor hydroxamic acid preparation; neutrophil collagenase inhibitor hydroxamic acid preparation; gelatinase inhibitor hydroxamic acid preparation.

Modifications around the dipeptide-mimetic core of hydroxamic acid based matrix metalloproteinase inhibitors I [AA = L-Trp, D-Trp, L-Trp(Me), L-3-benzothienylalanine, L-1- and -2-naphthylalanine, L-3- and -8-quinolylalanine, L-4-phenylphenylalanine, L-Phe, L-3- and -4-pyridylalanine, L-tert-leucine, L-abrine; R6 = NHMe, NH(CH2)4Me, NHCH2CH2OH, NHCH2CH2NHCO2CH2Ph, cyclopropylamino, cyclopentylamino, (S)- and (R)-1-indanylamino, (1R,2S)- and (1S,2R)-2-hydroxy-1-indanylamino, (S)-NHCHMePh, NHCH2Ph, piperonylamino, 2-, 3-, and 4-pyridylmethylamino, 2-(4-pyridyl)ethylamino, NHCH2CH2C6H4OH-4, 2-furanylmethylamino, 2-thiazolylmethylamino, 2-benzimidazolylamino, 3-(1-imidazolyl)propylamino, 3-(4-morpholinyl)propylamino; R2 = H, OH; R3 = CH2CHMe2, Bu, n-hexyl, n-octyl, OCHMe2, O(CH2)4Me] were studied. These variations incorporated a variety of natural, unnatural, and synthetic amino acids in addition to modifications of the P1′ and P3′ substituents. The results of this study indicate the following structural requirements: (1) Two key hydrogen bonds must be present between the enzyme and potent substrates. (2) Potent inhibitors must possess potent zinc-binding functionalities. (3) The potential importance of the hydrophobic group at position R3 as illustrated by its ability to impart greater relative potency against stromelysin when larger hydrophobic groups are used. (4) Requirements surrounding the nature of the amino acid appear to be more restrictive for stromelysin than for neutrophil collagenase, 72 kDa gelatinase, and 92 kDa gelatinase. These requirements may involve planar fused-ring aryl systems and possibly hydrogen-bonding capabilities.

Journal of Medicinal Chemistry published new progress about Hydroxamic acids Role: BAC (Biological Activity or Effector, Except Adverse), BSU (Biological Study, Unclassified), SPN (Synthetic Preparation), BIOL (Biological Study), PREP (Preparation). 617-55-0 belongs to class esters-buliding-blocks, and the molecular formula is C6H10O5, Application of C6H10O5.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Tymtsunik, Andriy V.; Kokhan, Serhii O.; Ivon, Yevhen M.; Komarov, Igor V.; Grygorenko, Oleksandr O. published the artcile< Intramolecular functional group differentiation as a strategy for the synthesis of bridged bicyclic β-amino acids>, Name: (S)-Dimethyl 2-hydroxysuccinate, the main research area is nipecotic acid analog beta amino acid bridged bicyclic preparation.

Differentiation of identical electrophilic functional groups (carboxylates) by a strategically placed internal nucleophile (an amino group) in cyclic precursors was used as a key general approach to functionalized azabicyclic scaffolds. The utility of the method was demonstrated by the synthesis of three bicyclic β-amino acids (analogs of nipecotic acid), which were prepared in good yields and on a relatively large scale.

RSC Advances published new progress about Bicyclic compounds Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation) (aza-). 617-55-0 belongs to class esters-buliding-blocks, and the molecular formula is C6H10O5, Name: (S)-Dimethyl 2-hydroxysuccinate.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Critcher, Douglas; Pattenden, Gerald published the artcile< Synthetic studies towards pateamine, a novel thiazole-based 19-membered bis-lactone from Mycale sp>, Reference of 617-55-0, the main research area is pateamine lactone preparation.

A concise synthesis of the 19-membered bis-lactone core I present in pateamine using chiral pool starting materials and featuring an intramol. Stille coupling reaction as a key stratagem, is described.

Tetrahedron Letters published new progress about 617-55-0. 617-55-0 belongs to class esters-buliding-blocks, and the molecular formula is C6H10O5, Reference of 617-55-0.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Dean, Jacob C.; Kusaka, Ryoji; Walsh, Patrick S.; Allais, Florent; Zwier, Timothy S. published the artcile< Plant Sunscreens in the UV-B: Ultraviolet Spectroscopy of Jet-Cooled Sinapoyl Malate, Sinapic Acid, and Sinapate Ester Derivatives>, HPLC of Formula: 617-55-0, the main research area is plant UV B UV spectroscopy jet cold sinapate derivative.

UV spectroscopy of sinapoyl malate, an essential UV-B screening agent in plants, was carried out in the cold, isolated environment of a supersonic expansion to explore its intrinsic UV spectral properties in detail. Despite these conditions, sinapoyl malate displays anomalous spectral broadening extending well over 1000 cm-1 in the UV-B region, presenting the tantalizing prospect that nature’s selection of UV-B sunscreen is based in part on the inherent quantum mech. features of its excited states. Jet-cooling provides an ideal setting in which to explore this topic, where complications from intermol. interactions are eliminated. In order to better understand the structural causes of this behavior, the UV spectroscopy of a series of sinapate esters was undertaken and compared with ab initio calculations, starting with the simplest sinapate chromophore sinapic acid, and building up the ester side chain to sinapoyl malate. This “”deconstruction”” approach provided insight into the active mechanism intrinsic to sinapoyl malate, which is tentatively attributed to mixing of the bright V (1ππ*) state with an adiabatically lower 1nπ* state which, according to calculations, shows unique charge-transfer characteristics brought on by the electron-rich malate side chain. All members of the series absorb strongly in the UV-B region, but significant differences emerge in the appearance of the spectrum among the series, with derivatives most closely associated with sinapoyl malate showing characteristic broadening even under jet-cooled conditions. The long vibronic progressions, conformational distribution, and large oscillator strength of the V (ππ*) transition in sinapates makes them ideal candidates for their role as UV-B screening agents in plants.

Journal of the American Chemical Society published new progress about Ab initio methods. 617-55-0 belongs to class esters-buliding-blocks, and the molecular formula is C6H10O5, HPLC of Formula: 617-55-0.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Tandon, Vishnu K.; Van Leusen, Albert M.; Wynberg, Hans published the artcile< Synthesis of enantiomerically pure (S)-(+)-3-hydroxytetrahydrofuran, and its (R)-enantiomer, from malic or tartaric acid>, Safety of (S)-Dimethyl 2-hydroxysuccinate, the main research area is furanol tetrahydro enantiomer; hydroxytetrahydrofuran enantiomer; butanetriol cyclodehydration.

The title compounds [(S)- and (R)-I] were prepared in high yield and high enantiomeric purity by cyclodehydration of (S)- and (R)-1,2,4-butanetriol, resp. Thus, (S)-HO2CCH(OH)CH2CO2H was esterified and reduced with LiAlH4 to give the (S)-triol, which was treated with 4-MeC6H4SO3H to give 87% (S)-I.

Journal of Organic Chemistry published new progress about Cyclization. 617-55-0 belongs to class esters-buliding-blocks, and the molecular formula is C6H10O5, Safety of (S)-Dimethyl 2-hydroxysuccinate.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Schleicher, Kristin D.; Jamison, Timothy F. published the artcile< A reductive coupling strategy towards ripostatin A>, COA of Formula: C6H10O5, the main research area is ripostatin A synthesis reductive coupling enyne epoxide; catalysis; natural product; nickel; reductive coupling; ripostatin A; synthesis.

Synthetic studies on the antibiotic natural product ripostatin A have been carried out with the aim to construct the C9-C10 bond by a nickel(0)-catalyzed coupling reaction of an enyne and an epoxide, followed by rearrangement of the resulting dienylcyclopropane intermediate to afford the skipped 1,4,7-triene. A cyclopropyl enyne fragment, I, corresponding to C1-C9 has been synthesized in high yield and demonstrated to be a competent substrate for the nickel(0)-catalyzed coupling with a model epoxide. Several synthetic approaches toward the C10-C26 epoxide have been pursued. The C13 stereocenter can be set by allylation and reductive decyanation of a cyanohydrin acetonide. A mild, fluoride-promoted decarboxylation enables construction of the C15-C16 bond by an aldol reaction. The product of this transformation, ketone II, is of the correct oxidation state and potentially three steps removed from the targeted epoxide fragment.

Beilstein Journal of Organic Chemistry published new progress about Reductive coupling reaction. 617-55-0 belongs to class esters-buliding-blocks, and the molecular formula is C6H10O5, COA of Formula: C6H10O5.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Critcher, Douglas; Pattenden, Gerald published the artcile< Synthetic studies towards pateamine, a novel thiazole-based 19-membered bis-lactone from Mycale sp>, Reference of 617-55-0, the main research area is pateamine lactone preparation.

A concise synthesis of the 19-membered bis-lactone core I present in pateamine using chiral pool starting materials and featuring an intramol. Stille coupling reaction as a key stratagem, is described.

Tetrahedron Letters published new progress about 617-55-0. 617-55-0 belongs to class esters-buliding-blocks, and the molecular formula is C6H10O5, Reference of 617-55-0.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Dean, Jacob C.; Kusaka, Ryoji; Walsh, Patrick S.; Allais, Florent; Zwier, Timothy S. published the artcile< Plant Sunscreens in the UV-B: Ultraviolet Spectroscopy of Jet-Cooled Sinapoyl Malate, Sinapic Acid, and Sinapate Ester Derivatives>, HPLC of Formula: 617-55-0, the main research area is plant UV B UV spectroscopy jet cold sinapate derivative.

UV spectroscopy of sinapoyl malate, an essential UV-B screening agent in plants, was carried out in the cold, isolated environment of a supersonic expansion to explore its intrinsic UV spectral properties in detail. Despite these conditions, sinapoyl malate displays anomalous spectral broadening extending well over 1000 cm-1 in the UV-B region, presenting the tantalizing prospect that nature’s selection of UV-B sunscreen is based in part on the inherent quantum mech. features of its excited states. Jet-cooling provides an ideal setting in which to explore this topic, where complications from intermol. interactions are eliminated. In order to better understand the structural causes of this behavior, the UV spectroscopy of a series of sinapate esters was undertaken and compared with ab initio calculations, starting with the simplest sinapate chromophore sinapic acid, and building up the ester side chain to sinapoyl malate. This “”deconstruction”” approach provided insight into the active mechanism intrinsic to sinapoyl malate, which is tentatively attributed to mixing of the bright V (1ππ*) state with an adiabatically lower 1nπ* state which, according to calculations, shows unique charge-transfer characteristics brought on by the electron-rich malate side chain. All members of the series absorb strongly in the UV-B region, but significant differences emerge in the appearance of the spectrum among the series, with derivatives most closely associated with sinapoyl malate showing characteristic broadening even under jet-cooled conditions. The long vibronic progressions, conformational distribution, and large oscillator strength of the V (ππ*) transition in sinapates makes them ideal candidates for their role as UV-B screening agents in plants.

Journal of the American Chemical Society published new progress about Ab initio methods. 617-55-0 belongs to class esters-buliding-blocks, and the molecular formula is C6H10O5, HPLC of Formula: 617-55-0.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Tandon, Vishnu K.; Van Leusen, Albert M.; Wynberg, Hans published the artcile< Synthesis of enantiomerically pure (S)-(+)-3-hydroxytetrahydrofuran, and its (R)-enantiomer, from malic or tartaric acid>, Safety of (S)-Dimethyl 2-hydroxysuccinate, the main research area is furanol tetrahydro enantiomer; hydroxytetrahydrofuran enantiomer; butanetriol cyclodehydration.

The title compounds [(S)- and (R)-I] were prepared in high yield and high enantiomeric purity by cyclodehydration of (S)- and (R)-1,2,4-butanetriol, resp. Thus, (S)-HO2CCH(OH)CH2CO2H was esterified and reduced with LiAlH4 to give the (S)-triol, which was treated with 4-MeC6H4SO3H to give 87% (S)-I.

Journal of Organic Chemistry published new progress about Cyclization. 617-55-0 belongs to class esters-buliding-blocks, and the molecular formula is C6H10O5, Safety of (S)-Dimethyl 2-hydroxysuccinate.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Schleicher, Kristin D.; Jamison, Timothy F. published the artcile< A reductive coupling strategy towards ripostatin A>, COA of Formula: C6H10O5, the main research area is ripostatin A synthesis reductive coupling enyne epoxide; catalysis; natural product; nickel; reductive coupling; ripostatin A; synthesis.

Synthetic studies on the antibiotic natural product ripostatin A have been carried out with the aim to construct the C9-C10 bond by a nickel(0)-catalyzed coupling reaction of an enyne and an epoxide, followed by rearrangement of the resulting dienylcyclopropane intermediate to afford the skipped 1,4,7-triene. A cyclopropyl enyne fragment, I, corresponding to C1-C9 has been synthesized in high yield and demonstrated to be a competent substrate for the nickel(0)-catalyzed coupling with a model epoxide. Several synthetic approaches toward the C10-C26 epoxide have been pursued. The C13 stereocenter can be set by allylation and reductive decyanation of a cyanohydrin acetonide. A mild, fluoride-promoted decarboxylation enables construction of the C15-C16 bond by an aldol reaction. The product of this transformation, ketone II, is of the correct oxidation state and potentially three steps removed from the targeted epoxide fragment.

Beilstein Journal of Organic Chemistry published new progress about Reductive coupling reaction. 617-55-0 belongs to class esters-buliding-blocks, and the molecular formula is C6H10O5, COA of Formula: C6H10O5.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics