Electron-transfer substitution reactions: Facilitation by the cyano group

Kornblum, Nathan; Fifolt, Michael J.

doi:10.1016/0040-4020(89)80129-2

Cited by 18 publications

(9 citation statements)

References 18 publications

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“…known compound; white solid (19 mg, 29% yield); 1 H NMR (300 MHz, CDCl 3 ) δ 10.05 (s, 1H), 7.96 (d, J = 8.3 Hz, 2H), 7.81 (d, J = 8.3 Hz, 2H); 13 C NMR (75 MHz, CDCl 3 ) δ 190.9, 138.8, 133.0, 130.0, 117.9, 117.6.…”

Section: Methodsmentioning

confidence: 99%

π-Conjugated Triazenes: Intermediates That Undergo Oxidation and Substitution Reactions

Barragan

Bugarin

2017

J. Org. Chem.

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Novel reactivity for π-conjugated triazenes is herein reported. This observed and unprecedented triazene reactivity gave access to oxidation and substitution reactions. These transformations include successful synthesis of aldehydes, ketones, ethers, and sulfides from readily available organic azides via π-conjugated triazene intermediates. Notably, the afforded adducts were obtained in good yields, at room temperature, and in the absence of added metal catalysts.

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Section: Methodsmentioning

confidence: 99%

π-Conjugated Triazenes: Intermediates That Undergo Oxidation and Substitution Reactions

Barragan

Bugarin

2017

J. Org. Chem.

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“…The radioligand concentrations were: [ 3 H]CCPA, 0.5 n m (rat and human A 1 ); [ 3 H]MSX‐2 1.0 n m (rat and human A 2A ); [ 3 H]PSB‐603, 0.3 n m (rat and human A 2B ); [ 3 H]PSB‐11, 0.5 n m (human A 3 ); [ 3 H]NECA, 10 n m (rat A 3 ). Binding assays were performed as described previously . About 30–70 μg mL −1 of protein were used in the assays.…”

Section: Methodsmentioning

confidence: 99%

“…Binding assays were performed as described previously [20,. 21,23,32,33] About 30-70 mgmL À1 of protein were used in the assays. At least three separate experiments were performed, each in duplicate or triplicate.…”

mentioning

confidence: 99%

2‐Amino[1,2,4]triazolo[1,5‐c]quinazolines and Derived Novel Heterocycles: Syntheses and Structure–Activity Relationships of Potent Adenosine Receptor Antagonists

et al. 2016

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2-Amino[1,2,4]triazolo[1,5-c]quinazolines were identified as potent adenosine receptor (AR) antagonists. Synthetic strategies were devised to gain access to a broad range of derivatives including novel polyheterocyclic compounds. Potent and selective A AR antagonists were discovered, including 3,5-diphenyl[1,2,4]triazolo[4,3-c]quinazoline (17, K human A AR 1.16 nm) and 5'-phenyl-1,2-dihydro-3'H-spiro[indole-3,2'-[1,2,4]triazolo[1,5-c]quinazolin]-2-one (20, K human A AR 6.94 nm). In addition, multitarget antagonists were obtained, such as the dual A /A antagonist 2,5-diphenyl[1,2,4]triazolo[1,5-c]quinazoline (13 b, K human A AR 51.6 nm, human A AR 11.1 nm), and the balanced pan-AR antagonists 5-(2-thienyl)[1,2,4]triazolo[1,5-c]quinazolin-2-amine (11 c, K human A AR 131 nm, A AR 32.7 nm, A AR 150 nm, A AR 47.5 nm) and 9-bromo-5-phenyl[1,2,4]triazolo[1,5-c]quinazolin-2-amine (11 q, K human A AR 67.7 nm, A AR 13.6 nm, A AR 75.0 nm, A AR 703 nm). In many cases, significantly different affinities for human and rat receptors were observed, which emphasizes the need for caution in extrapolating conclusions between different species.

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“…Scheme 3 depicts the sequence of reactions that led to the preparation of compounds 3a,b using 1,3-dimethyl-4-nitrobenzene, 14, as the starting material. Compound 15 27 was synthesized by KMnO 4 -promoted oxidation of methyl groups in 14, followed by esterification and selective hydrolysis, a procedure developed by Axer. 28 After chlorination of acid and N-acylation, compound 19 was obtained, and then 19 was reduced by Sn in the mixture of hydrochloric acid and ethanol to give 20.…”

Section: Focused Combinatorial Library Design and Virtualmentioning

confidence: 99%

Strategy for Discovering Chemical Inhibitors of Human Cyclophilin A: Focused Library Design, Virtual Screening, Chemical Synthesis and Bioassay

Zhang

Chen

et al. 2006

J. Comb. Chem.

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The discovery of cyclophilin A (CypA) inhibitor is now of special interest in the treatment of immunological disorders. In this work, using a strategy integrating focused combinatorial library design, virtual screening, chemical synthesis, and bioassay, a series of novel small molecular CypA inhibitors have been discovered. First, using the fragments taken from our previously discovered CypA inhibitors (Bioorg. Med. Chem. 2006, 14, 2209-2224) as building blocks, we designed a focused combinatorial library containing 255 molecules employing the LD1.0 program (J. Comb. Chem. 2005, 7, 398-406) developed by us. Sixteen compounds (1a-e, 2a-b, 3a-b, and 4a-g) were selected by using virtual screening against the X-ray crystal structure of CypA as well as druglike analysis for further synthesis and bioassay. All these sixteen molecules are CypA binders with binding affinities (K(D) values) ranging from 0.076 to 41.0 microM, and five of them (4a, 4c, and 4e-g) are potent CypA inhibitors with PPIase inhibitory activities (IC(50) values) of 0.25-6.43 microM. The hit rates for binders and inhibitors are as high as 100% and 31.25%, respectively. Remarkably, both the binding affinity and inhibitory activity of the most potent compound increase approximately 10 times than that of the most active compound discovered previously. The high hit rate and the high potency of the new CypA inhibitors demonstrated the efficiency of the strategy for focused library design and screening. In addition, the novel chemical entities reported in this study could be leads for discovering new therapies against the CypA pathway.

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Electron-transfer substitution reactions: Facilitation by the cyano group

Cited by 18 publications

References 18 publications

π-Conjugated Triazenes: Intermediates That Undergo Oxidation and Substitution Reactions

π-Conjugated Triazenes: Intermediates That Undergo Oxidation and Substitution Reactions

2‐Amino[1,2,4]triazolo[1,5‐c]quinazolines and Derived Novel Heterocycles: Syntheses and Structure–Activity Relationships of Potent Adenosine Receptor Antagonists

Strategy for Discovering Chemical Inhibitors of Human Cyclophilin A: Focused Library Design, Virtual Screening, Chemical Synthesis and Bioassay

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