Nucleophilic substitution reaction at an sp2 carbon of vinyl halides with an intramolecular thiol moiety: synthesis of thio-heterocycles

Lei, Mao-Yi; Xiao, Yongjun; Liu, Weimin; Fukamizu, Koji; Chiba, Shunsuke; Ando, Kaori; Narasaka, Koichi

doi:10.1016/j.tet.2009.06.078

Cited by 36 publications

(10 citation statements)

References 53 publications

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“…Protein binding alerts for skin sensitization by OASIS profilers categorized DDVP as a strong sensitizer based on nucleophilic substitution reaction on vinyl (sp 2 ) carbon atom. Chemical compounds with these alerts are capable of reacting covalently with proteins via a S N Vinyl reaction at a sp 2 carbon atom [ 44 ].…”

Section: Resultsmentioning

confidence: 99%

Assessment of the cytotoxic and mutagenic potential of dichlorvos (DDVP) using in silico classification model; a health hazard awareness in Nigeria

Abaukaka

Sanusi

Abdullahi

et al. 2020

Environ Anal Health Toxicol

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Dichlorvos (DDVP) has been abused in Nigeria for suicide attempts, topical applications to treat an ectoparasitic infestation, and indiscriminate use on farm produce. Exposure to this compound in subacute concentration can cause toxicity in different tissues by alteration of the cellular antioxidative defence mechanism. This analysis is aimed at the systematic profiling of DDVP to assess its cytotoxic and mutagenic potential for human vulnerability using an in silico classification model. DDVP was grouped into categories of analogue chemical compounds generated from inventories based on structural alerts that measure the biological effects on cell lines and animal models using the quantitative structure-activity relationship (QSAR) model. The cytotoxic and mutagenic potential of DDVP was assessed by analyzing target endpoints like skin sensitization, oral/inhalation toxicity, neurotoxicity and mutagenicity. DDVP shows moderate sensitization potential that can induce skin irritation during prolonged exposure because of the presence of dichlorovenyl side-chain that interacts with cellular proteins and causes degradation. 50% lethal dose (LD 50 ) of DDVP per body weight was determined to be 26.2 mg/kg in a rat model at 95% confidence range for acute oral toxicity, and 14.4 mmol/L was estimated as 50% lethal concentration (LC 50 ) in the atmosphere due to acute inhalation toxicity. DDVP can also inhibit acetylcholinesterase in the nervous system to produce nicotinic and muscarinic symptoms like nausea, vomiting, lacrimation, salivation, bradycardia, and respiratory failure may cause death. The widely used pesticide causes weak DNA methylation which can repress gene transcription on promoter sites. DDVP is volatile so it can cause oral and inhalation toxicity coupled with neurotoxicity during prolonged exposure. Serum cholinesterase blood tests should be encouraged in federal and state hospitals to investigate related health challenges as DDVP is still used in Nigeria.

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Section: Resultsmentioning

confidence: 99%

Assessment of the cytotoxic and mutagenic potential of dichlorvos (DDVP) using in silico classification model; a health hazard awareness in Nigeria

Abaukaka

Sanusi

Abdullahi

et al. 2020

Environ Anal Health Toxicol

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“…On the other hand, when compound 4 was allowed to react with sodium cyanide in ethanol, compound 2 was obtained (Figure 3). 22,32 The 13 C NMR spectrum of compound 2 exhibited three characteristic signals at δ 102.3, 109.1, and 137.4 ppm corresponding to C-5, C≡N, and C-4, respectively. Moreover, treatment of ethyl ester 3 with equivalent amounts of piperidine and morpholine in boiling ethanol yielded 2-amino-3-(piperidin/morpholin-1-ylcarbonyl)-6H -1-benzoxocin-6-ones 9 and 10, respectively (Figure 3).…”

Section: Resultsmentioning

confidence: 99%

Ring opening and ring closure reactions of chromone-3-carboxylic acid: unexpected routes to synthesize functionalized benzoxocinones and heteroannulated pyranochromenes

Ibrahim¹,

Ali²

2015

Turk J Chem

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Unexpected routes to synthesize functionalized benzoxocinones and heteroannulated pyranochromenes were achieved via transformations of the γ -pyrone ring in chromone-3-carboxylic acid throughout its reactions with some acyclic and cyclic carbon nucleophiles. A key part of the reaction mechanisms is discussed. Structures of the new synthesized products were established on the basis of elemental analysis and spectral data (IR, MS, and 1 H and 13 C NMR).

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“…The method was applied using various substrates to synthesize a series of 2-alkylidenethietanes 528-532. The S-(2,7-dibromoocta-1,7-dien-4-yl)thioacetate (527) generated the 2-methylidenethietane derivative 532 exclusively under the reaction conditions, revealing that the reaction preferred the 4-exo ring closure [153,154] (Scheme 123). In 2009, Li and his co-workers developed a ligand-free CuI-catalyzed intramolecular S-vinylation of 2-bromo/chloroalk-1-ene-4-thiols 533-539 for the preparation of 2-alkylidenethietanes 528, 532, and 540-544.…”

Section: Synthesis Via the Intramolecular Nucleophilic Substitution Omentioning

confidence: 99%

Recent synthesis of thietanes

Xu¹

2020

Beilstein J. Org. Chem.

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Thietanes are important aliphatic four-membered thiaheterocycles that are found in the pharmaceutical core and structural motifs of some biological compounds. They are also useful intermediates in organic synthesis. Various synthetic methods of thietanes have been developed, including inter- and intramolecular nucleophilic thioetherifications, photochemical [2 + 2] cycloadditions, ring expansions and contractions, nucleophilic cyclizations, and some miscellaneous methods. The recently developed methods provide some new strategies for the efficient preparation of thietanes and their derivatives. This review focuses on the synthetic methods to construct thietane backbones developed during 1966 to 2019.

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Nucleophilic substitution reaction at an sp2 carbon of vinyl halides with an intramolecular thiol moiety: synthesis of thio-heterocycles

Cited by 36 publications

References 53 publications

Assessment of the cytotoxic and mutagenic potential of dichlorvos (DDVP) using in silico classification model; a health hazard awareness in Nigeria

Assessment of the cytotoxic and mutagenic potential of dichlorvos (DDVP) using in silico classification model; a health hazard awareness in Nigeria

Ring opening and ring closure reactions of chromone-3-carboxylic acid: unexpected routes to synthesize functionalized benzoxocinones and heteroannulated pyranochromenes

Recent synthesis of thietanes

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