• Title/Summary/Keyword: Thione

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A Highly Stereoselective Reaction in Aminolysis of 3-Acyl-4-(S)-isopropyl-1,3-thiazolidine-2-thione with Racemic Amines (3-Acyl-4(S)-isopropyl-1,3-Thiazolidine-2-Thione과 라세미아민의 입체선택적인 반응)

  • Tae Myoung Jeong;Ki Hun Park
    • Journal of the Korean Chemical Society
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    • v.32 no.6
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    • pp.588-592
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    • 1988
  • A chiral recognition was observed in aminolysis of 3-acyl-4(S)-isopropyl-1,3-thiazolidine-2-thione by racemic amine to give an optically active amide (S-excess) and amine (R-excess). This procedure can be applied to synthesis of macrocyclic diamide macrocyclic spermidine alkaloid, and peptide. The rate of this aminolysis is remarkably affected by steric surrounding; completion of reaction can be easily judged by the disappearance of the original yellow color of 4(S)-AITT. These features of the aminolysis suggested a potential recognition racemic amines by a chiral 4 (S)-AITT derivative. Thus 4 (S)-AITT was synthesized from 4 (S)-isopropyl-1, 3-thiazolidine-2-thione and carboxylic acids.

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Thiadiazole-thione surfactants: Preparation, flotation performance and adsorption mechanism to malachite

  • Huang, Yaoguo;Liu, Guangyi;Liu, Jun;Yang, Xianglin;Zhang, Zhiyong
    • Journal of Industrial and Engineering Chemistry
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    • v.67
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    • pp.99-108
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    • 2018
  • In this paper, novel thiadiazole-thione surfactants including 5-heptyl-1,3,4-thiadiazole-2-thione (HpSDT), 5-phenyl-1,3,4-thiadiazole-2-thione (PSDT) and 5-(2-hydroxyphenyl)-1,3,4-thiadiazole-2-thione (HPhSDT) were synthesized and originally introduced as collectors in froth flotation. Microflotation tests showed that HpSDT exhibited better flotation response to malachite than PSDT and HPhSDT, as well as excellent flotation selectivity against quartz. The contact angle results inferred that the hydrophobization intensity of these collectors toward malachite was in the order as HpSDT> PSDT> HPhSDT. ${\zeta}$-potential recommended a chemisorption of HpSDT on malachite surfaces. FTIR deduced that cupric or cuprous atoms might bond with the S and N atoms of HpSDT to form a conjugated ring. XPS further gave an additional evidence that HpSDT-Cu(I) complexes were produced on malachite surfaces via combining surface Cu atoms with HpSDT's N and S atoms, with reducing surface Cu(II) to Cu (I). The tighter orientation arrangement on malachite and stronger hydrophobicity rendered HpSDT to possess better flotation affinity toward malachite than PSDT and HPhSDT.

Study on 4,4-pentamethylene-1,3-oxazolidine-5-one-2-thione (4,4-pentamethylene-1,3-oxazolidine-5-one-2-thione에 관한 연구)

  • 국채호;조윤상;주상섭
    • YAKHAK HOEJI
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    • v.16 no.2
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    • pp.85-89
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    • 1972
  • 4,4-Pentamethylene-1,3-oxazolidine-5-one-2-thione is to be obtained from 1-amino cyclohexane carboxylic acid and thiophosgene, however, it was not isolated because of its unstability. When it was treated with $C_{6}H_{5}NH_{2},$ N-phenyl-(1-aminocyclohexane) carboxylic acid and N-(1-carboxycyclohexyl), N-phenyl thiourea were obtained. When refluxed in $H_{2}O$ at pH 2, pH 12 and neutral condition, the resulting carboxylic compound, being anticipated by us, was 1-aminocyclohexane carboxylic acid. From the above results, we have got the suggestion f the chemical behavior of 4,4-pentamethylene-1,3-oxazolidine-5-one-2-thione and also some informations of the reaction mechanism between 1-aminocyclohexane carboxylic acid and thiophosgene.

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Theoritical Studies on Structure of 4H-Pyran-4-one and Its Sulfur Analogues (4H-Pyran-4-one과 그의 황 유도체의 구조에 관한 이론적 연구)

  • Ikchoon Lee;Hyeong Yeoun Park;Young Ki Kim
    • Journal of the Korean Chemical Society
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    • v.30 no.6
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    • pp.495-499
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    • 1986
  • Structures of 4H-pyran-4-one(I), 4H-pyran-4-thione(II), 4H-thiapyran-4-one (III), 4H-thiapyran-4-thione(IV) have been determined by MNDO and MINDO/3 methods. Geometries and physicochemical properties, especially the aromaticity, were found to agree well with the results of microwave experiments. The order of aromaticity was found to be (IV) > (III) > (II) > (I), which demonstrated inhibitory effect of strongly electronegative oxygen atom on the electron delocaligation, and the order of dipole moment, (II) > (IV) > (I) > (III), indicated the dominant contribution of the bond length of carbonyl group (C=O or C=S)

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Synthesis of 1-Aryl-2-mercapto-4-aryl-1,6-dihydro-1,3,5-triaszine-6-thione and their Latentiation Products as Antithyroidal Agent

  • Methrotra, S.;Roychowdhury, P.K.;Pandey, K.K.;Srivastava, P.K.
    • Archives of Pharmacal Research
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    • v.18 no.5
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    • pp.356-360
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    • 1995
  • Two new 1-aryl-2-benzylmercapto-4-aryl-1,6-dihydro-1,3,5-triazine-6-thiones hvae been synthesized by known methods (Coerdeler et al., 1967). These triazines on treatment with thiourea as dealkylating agent, in acidic medium afforded the corresponding 1-ary-2-mercapto-4-aryl-1,6-dihydro-1,3,5-triazine-6-thione which on further reaction with different ${\alpha},{\;}{\beta}-unstaturated$ carbonyl compounds and aryl-cyanamide ydrochloride affordered the related adducts. Some of these compounds show appreciable antithyroidal activity.

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Acid and Base Catalyzed Intramolecular Cyclizations of N-Benzoylthiocarbamoyl-acetals

  • Lee, Bong-Yong;Kim, Choong-Sup;Lee, Jong-Wook
    • Archives of Pharmacal Research
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    • v.23 no.2
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    • pp.99-103
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    • 2000
  • Acid and base catalyzed intramolecular cyclizations of N-benzoylthioureidoacetal, contain-ing four functional groups adjacent to thiourea such as benzocarbamoyl, acetal, thioure and amide, were investigated. The condensation reaction of N-benzoyl thiocarbamoylgly-cine amide in the presence of 10% aqueous NaOH provided 1-(2,2-dimethoxy)ethyl-imi- dazolidine-2-thione exclusively. In the presence of pyridine, it was transformed to 2- thiohydantoin. N-Benzoyl thiocarbamoyl glycine amide was completely transformed to an iminothiazolidine exclusively in the presence of Lewis acid such as borontrifluoride ether-ate or trimethylsilyl iodide. 1-(2,2-Dimethoxy)ethyl-imidazolidine-2-thione was transformed to imidazole[2,1-b]thiazole and pyrazino[5,1-a]imidazole in the presence of $BF_3$.$ET_2$O and formic acid, respectively.

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Microwave Assisted N-Alkenyl Condensation between Pyrrolidine-2-thione and Various Aldehydes

  • Kim, Ki-Won;Lee, Ho-Joon;Kim, Chung-Gi;Park, Mi-Ja;Kwon, Tae-Woo
    • Bulletin of the Korean Chemical Society
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    • v.29 no.3
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    • pp.604-608
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    • 2008
  • A series of N-alkenyl pyrrolidine-2-thiones were synthesized by the reaction between pyrrolidine-2-thione and various aldehydes such as n-propanal, isopropanal, n-butanal, n-hexanal, n-octanal and phenylacetaldehyde in 32-86% yields using microwave irradiation technique. Only one structural E isomers were predominantly formed within 15 minutes in chlorobenezene?/p-toluenesulfonic acid monohydrate.

Synthesis of Mannich Base of Benzoxazolin-2-thione and Alkyl Ester of PAS and Their Antimicrobial Activities (Benzoxazolin-2-thione과 PAS의 Alkyl Ester과의 Mannich Base 합성 및 항균력에 관한 연구)

  • 정원근;정상헌;정필근;윤원영;이남복
    • YAKHAK HOEJI
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    • v.18 no.4
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    • pp.243-248
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    • 1974
  • Nine benzoxazolin-2-thione derivatives were sunthesized as the potential antimicrobial substances. These compounds were tested for the antimicrobial activities using Staphylococcus aureus and Escherichia coli by way of tube dilution method. The three compounds of I, II and VII omjoboted the growth of S.aureus at the concentration of 1${\mu}$g/ml, and III,VI,VIII and IX exhibited considerable antimicrobial activities against S. aureus at the concentration of 10.m.u.g/ml. As to the growth of E. Coli, VII VII and VIII inhibited at the concentration of 1${\mu}$g/,l. II,III and IV exhibited considerable antimicrobial activities against E. coli at the concentration of 10${\mu}$g/ml.

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1,3,4-Oxadiazole-2(3H)-thione as a New Scaffold for Pim Kinase Inhibitors

  • Lee, Ah Yeon;Hong, Victor Sukbong;Lee, Jinho
    • Quantitative Bio-Science
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    • v.37 no.2
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    • pp.113-124
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    • 2018
  • Pim kinases are important targets for cancer therapies because they are mainly responsible for cancer metastasis and overall therapeutic treatment responses. Because of their unusual structural feature in the hinge region of the ATP-binding site, new binding motifs have been discovered and used for the development of Pim kinases inhibitors. The results of a screening of 5-membered heteroaromatic compounds and the effects of structural modifications on the inhibition of Pim kinases' activities showed the potential scaffold for Pim inhibitors. 1,3,4-Oxadiazole-2(3H)-thione was found as a new scaffold for Pim kinase inhibitors.