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Journal articles on the topic 'Γ-Hydroxy-γ-lactam'

Author: Grafiati

Published: 4 June 2021

Last updated: 8 February 2022

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1

Jo, Deokhee, and Sunkyu Han. "Biomimetic total synthesis of (±)-berkeleyamide D." Organic Chemistry Frontiers 4, no. 4 (2017): 506–9. http://dx.doi.org/10.1039/c6qo00812g.

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2

Sengoku, Tetsuya, Koki Makino, Ayumi Iijima, Toshiyasu Inuzuka та Hidemi Yoda. "Bifurcated synthesis of methylene-lactone- and methylene-lactam-fused spirolactams via electrophilic amide allylation of γ-phenylthio-functionalized γ-lactams". Beilstein Journal of Organic Chemistry 16 (13 листопада 2020): 2769–75. http://dx.doi.org/10.3762/bjoc.16.227.

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New synthetic methods for spirolactams bearing an α-methylene-γ-butyrolactone or its analogous methylene-lactam have been developed. The allylation of γ-phenylthio-functionalized γ-lactams with 2-(acetoxy)methyl acrylamides was accomplished by using 2.5 equivalents of NaH to give the corresponding adducts in excellent yields. The remaining phenylthio group was substituted with a hydroxy group by treatment with CuBr, and the resulting γ-hydroxyamides were cyclized under acidic conditions to afford the corresponding methylene-lactam-fused spirolactams in high yields. On the other hand, methylene-lactone-fused spirolactams could be delivered from the allyl adducts in high yields through a sequential N-Boc protection/desulfinative lactonization.

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3

Chopin, Nicolas, Shinya Iikawa, Julien Bosson та ін. "7-Chloro-4-aminoquinoline γ-hydroxy-γ-lactam derived-tetramates as a new family of antimalarial compounds". Bioorganic & Medicinal Chemistry Letters 26, № 21 (2016): 5308–11. http://dx.doi.org/10.1016/j.bmcl.2016.09.038.

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4

Kumar, Brijesh, Mushtaq A. Aga, Abdul Rouf, Bhahwal A. Shah та Subhash C. Taneja. "Common precursor strategy for the synthesis of bestatin, amprenavir intermediate and syn-4-hydroxy-5-phenyl-γ-lactam". RSC Adv. 4, № 33 (2014): 17206–9. http://dx.doi.org/10.1039/c4ra00205a.

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A synthetic strategy using α,β-unsaturated ester as a common precursor for the preparation of bestatin hydrochloride, an anticancer agent; 1,3-diaminoalcohol, an amprenavir intermediate and syn-4-hydroxy-5-phenyl-γ-lactam, an intermediate of bioactive molecules with good yields and excellent stereoselectivity is described.

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5

D. Lubell, William, Daniel J. St-Cyr та Thierry Maris. "Crystal-State Structure Analysis of β-Hydroxy-γ-lactam Constrained Ser/Thr Peptidomimetics". HETEROCYCLES 82, № 1 (2010): 729. http://dx.doi.org/10.3987/com-10-s(e)52.

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6

Lee, Nagum, Min Lee Yu, Hyeyeon Jun та Soo Y. Ko. "Extending the Synthetic Utilities of the Tandem Cyclic Sulfate Rearrangement-Opening Process: Synthesis of β-Hydroxy-γ-phenyl-γ-lactam". Bulletin of the Korean Chemical Society 37, № 12 (2016): 2091–93. http://dx.doi.org/10.1002/bkcs.11026.

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7

St-Cyr, Daniel J., Andrew G. Jamieson та William D. Lubell. "α-Amino-β-hydroxy-γ-lactam for Constraining Peptide Ser and Thr Residue Conformation". Organic Letters 12, № 8 (2010): 1652–55. http://dx.doi.org/10.1021/ol1000582.

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8

Procopiou, Panayiotis A., та Rona M. Highcock. "A novel oxidatitive rearrangement of a pentasubstituted pyrrole to an unsaturated hydroxy γ-lactam". J. Chem. Soc., Perkin Trans. 1, № 3 (1994): 245–47. http://dx.doi.org/10.1039/p19940000245.

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9

Cornut, Damien, Hugues Lemoine, Oleksandr Kanishchev та ін. "Incorporation of a 3-(2,2,2-Trifluoroethyl)-γ-hydroxy-γ-lactam Motif in the Side Chain of 4-Aminoquinolines. Syntheses and Antimalarial Activities". Journal of Medicinal Chemistry 56, № 1 (2012): 73–83. http://dx.doi.org/10.1021/jm301076q.

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10

PROCOPIOU, P. A., та R. M. HIGHCOCK. "ChemInform Abstract: A Novel Oxidative Rearrangement of a Pentasubstituted Pyrrole to an Unsaturated Hydroxy γ-Lactam." ChemInform 25, № 21 (2010): no. http://dx.doi.org/10.1002/chin.199421081.

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11

Xu, Xin-Ya, Xiao-Yong Zhang, Fei He, Jiang Peng, Xu-Hua Nong, and Shu-Hua Qi. "Two New Compounds from Gorgonian-associated Fungus Aspergillus sp." Natural Product Communications 8, no. 8 (2013): 1934578X1300800. http://dx.doi.org/10.1177/1934578x1300800808.

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One new γ-lactone derivative 5-hydroxy-3-isopropyl-4-methoxyfuranone (1) and one new lactam derivative dehydrated-marinamide (2), along with two known compounds marinamide (3) and marinamide methyl ester (4) were isolated from the fermentation broth of the marine gorgonian-associated fungus Aspergillus sp. SCSGAF0093. Their structures were elucidated on the basis of spectroscopic and spectrometric analysis. Compound 1 showed significant toxicity to brine shrimp (Artemia salina) with a median lethal concentration (LC50) of 1.25 μM, and 3 inhibited protein tyrosine phosphatase 1B (PTPlB) with a half maximal inhibitory concentration (IC50) of 23.3 μg/mL.

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12

Haldar, Pranab, та Jayanta K. Ray. "CAN mediated decarboxylative hydroxylation/alkoxylation of N-aryl-γ-lactam-carboxylic acids at room temperature: an easy access to N-aryl-α-hydroxy/alkoxy-γ-lactams". Tetrahedron Letters 49, № 22 (2008): 3659–62. http://dx.doi.org/10.1016/j.tetlet.2008.03.147.

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13

Otake, Shinya, Norihiro Ogawa, Yoshikazu Kitano, Keiji Hasumi, and Eriko Suzuki. "Isoprene Side-chain of SMTP is Essential for Soluble Epoxide Hydrolase Inhibition and Cellular Localization." Natural Product Communications 11, no. 2 (2016): 1934578X1601100. http://dx.doi.org/10.1177/1934578x1601100223.

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SMTPs, a family of natural small molecules that effectively treat ischemic stroke, are subject to clinical development. SMTPs enhance plasminogen activation and inhibit soluble epoxide hydrolase (sEH), leading to promotion of endogenous thrombolysis and anti-inflammation. The SMTP molecule consists of a tricyclic γ-lactam moiety, an isoprene side-chain, and an N-linked side-chain. Here, we investigate the yet-to-be-characterized function of the isoprene side-chain of SMTPs in sEH inhibition and cellular distribution. The results demonstrated that oxidative modification as well as truncation of the side-chain abolished epoxide hydrolase inhibition. The introduction of a terminal hydroxy group exceptionally unaffected epoxide hydrolase, but led to impaired cellular localization, resulting in diminution of cellular epoxide hydrolase inhibition. Thus, the isoprene side-chain of SMTP is an important pharmacophore for epoxide hydrolase inhibition and cellular localization.

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14

Barman, Gopa. "A facile synthesis of diformylated pyrroles by dehydroxylation of N-aryl-5-hydroxy-γ-lactam derivatives under Vilsmeier reaction conditions". Chemistry of Heterocyclic Compounds 51, № 10 (2015): 869–71. http://dx.doi.org/10.1007/s10593-015-1789-z.

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15

Haldar, Pranab, та Jayanta K. Ray. "ChemInform Abstract: CAN-Mediated Decarboxylative Hydroxylation/Alkoxylation of N-Aryl-γ-lactam-carboxylic Acids at Room Temperature: An Easy Access to N-Aryl-α-hydroxy/Alkoxy-γ-lactams." ChemInform 39, № 36 (2008). http://dx.doi.org/10.1002/chin.200836113.

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16

Geranurimi, Azade, Colin W. H. Cheng, Christiane Quiniou та ін. "Interleukin-1 Receptor Modulation Using β-Substituted α-Amino-γ-Lactam Peptides From Solid-Phase Synthesis and Diversification". Frontiers in Chemistry 8 (21 грудня 2020). http://dx.doi.org/10.3389/fchem.2020.610431.

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As a key cytokine mediator of inflammation, interleukin-1β (IL-1β) binds to the IL-1 receptor (IL-1R) and activates various downstream signaling mediators, including NF-κB, which is required for immune vigilance and cellular protection. Toward the development of IL-1-targeting therapeutics which exhibit functional selectivity, the all-D-amino acid peptide 1 (101.10, H-D-Arg-D-Tyr-D-Thr-D-Val-D-Glu-D-Leu-D-Ala-NH2) was conceived as an allosteric IL-1R modulator that conserves NF-κB signaling while inhibiting other IL-1-activated pathways. Employing β-hydroxy-α-amino-γ-lactam (Hgl) stereoisomers to study the conformation about the Thr3 residue in 1, [(3R,4S)-Hgl3]-1 (2b), among all possible diastereomers, was found to exhibit identical in vitro and in vivo activity as the parent peptide and superior activity to the α-amino-γ-lactam (Agl) counterpart. Noting the relevance of the β-hydroxyl substituent and configuration for the activity of (3R,4S)-2b, fifteen different β-substituted-Agl3 analogs of 1 (e.g., 2c-q) have now been synthesized by a combination of solution- and solid-phase methods employing N-Fmoc-β-substituted-Agl3-Val-OH dipeptide building blocks. Introduction of a β-azido-Agl3 residue into the resin bound peptide and subsequent reduction and CuAAC chemistry gave access to a series of amine and triazole derivatives (e.g., 2h-q). β-Substituted-[Agl3]-1 analogs 2c-q exhibited generally similar circular dichroism (CD) spectra as that of Hgl analog 2b in water, presenting curve shapes indicative of β-turn structures. The relevance of the β-substituent was indicated in rodent models of preterm labor and retinopathy of prematurity (ROP), in which certain analogs inhibited preterm birth and vaso-obliteration, respectively, with activity similar to 1 and 2b. The β-substituted-[Agl3]-1 analogs exhibited functional selectivity on IL-1-induced signaling pathways. The described solid-phase method has provided discerning probes for exploring peptide structure-activity relationships and valuable leads for developing prototypes to treat inflammatory events leading to prematurity and retinopathy of prematurity, which are leading causes of infant morbidity and blindness respectively.

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17

Barman, Gopa. "ChemInform Abstract: A Facile Synthesis of Diformylated Pyrroles by Dehydroxylation of N-Aryl-5-hydroxy-γ-lactam Derivatives under Vilsmeier Reaction Conditions." ChemInform 47, № 17 (2016). http://dx.doi.org/10.1002/chin.201617117.

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