• Title/Summary/Keyword: Trifluoromethyl

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Synthesis and Antiproliferative Activity of New Aminoisoquinolinylurea Derivatives against Melanoma Cell Line

  • Cho, Hye Jung;El-Gamal, Mohammed I.;Oh, Chang-Hyun;Lee, So Ha;Kim, Garam;Hong, Jun Hee;Choi, Hong Seok;Yoo, Kyung Ho
    • Bulletin of the Korean Chemical Society
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    • v.33 no.11
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    • pp.3635-3639
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    • 2012
  • A series of new diarylureas possessing aminoisoquinoline scaffold was synthesized, and their in vitro antiproliferative activity against A375P human melanoma cell line was tested. Compounds 1d, 1l, 1n, 1p, 1q, and 1t showed superior potency against A375P to Sorafenib. The highest potency was shown by compound 1p possessing 3,5-bis(trifluoromethyl)phenyl terminal ring with $IC_{50}$ value of $0.41{\mu}M$.

Synthesis and Preliminary Cytotoxicity Evaluation of New Diarylamides and Diarylureas Possessing 2,3-Dihydropyrrolo[3,2-b]quinoline Scaffold

  • Kim, Hyun-Jin;El-Gamal, Mohammed I.;Lee, Yong Sup;Oh, Chang-Hyun
    • Bulletin of the Korean Chemical Society
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    • v.34 no.8
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    • pp.2480-2486
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    • 2013
  • A new series of diarylamides and diarylureas having 2,3-dihydropyrrolo[3,2-b]quinoline scaffold was synthesized. Their in vitro antiproliferative activities were tested over NCI-60 cancer cell lines of nine different cancer types. Some target compounds showed good inhibition percentages over different cell lines. Among all the target compounds, compound 1f possessing 6,7-dimethoxy-2,3-dihydropyrrolo[3,2-b]quinoline nucleus, amide linker, and 4-chloro-3-(trifluoromethyl)phenyl terminal ring showed high selectivity against MCF7 and MDA-MB-468 breast cancer cell lines more than the other tested cell lines. Its inhibition percentages at $10{\mu}M$ concentration over those two cell lines were 84.97% and 87.13%, respectively.

Synthesis of New Pyrimidinylaminobenzene Derivatives and Their Antiproliferative Activities against Melanoma Cell Line

  • Kim, Hee Jin;Oh, Chang-Hyun;Yoo, Kyung Ho
    • Bulletin of the Korean Chemical Society
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    • v.34 no.8
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    • pp.2311-2316
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    • 2013
  • A series of new diarylamide and diarylurea derivatives possessing pyrimidinylaminobenzene scaffold was synthesized. Their in vitro antiproliferative activities were tested against A375P human melanoma cell line. Among them, compounds 1a-c, k and 2b-d, f, g, j, l showed superior potencies against A375P human melanoma cell line to Sorafenib. In particular, compound 2f possessing 3-fluoro-5-trifluoromethyl moiety exhibited the highest potency with $IC_{50}$ value in nanomolar scale.

Synthesis of New pyridyl Squarine Dyes and Application to Poly(vinyl cinnamoyl actate)(III) (신규 pyridyl Squarine Dyes의 합성 및 Poly(vinyl cinnamoyl actate)의 고감도화(III))

  • 손세모
    • Journal of the Korean Graphic Arts Communication Society
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    • v.18 no.2
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    • pp.143-151
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    • 2000
  • A previous paper was reported in being sensetized photopolymer, poly(vinyl cinnamoyl acetate)(PVCiA)$^{1.2)}$ with some squarylium dyes such as 1,3-bis(4 or 6-trifluoromethyl-1,3,3-trimethylindo)squarylium dyes(TFSQ) and 1,3-bis(4 or 6-nitro-1,3,3-trimethylindo)(NISQ). Here, we synthesized new 1,3-bis(1,3,3-trimethylpyridylindo)squarylium dyes(PSQD) to sensetize photopolymer, such as poly(vinyl cinnamoyl acetate). Absorption's coefficient of (PSQDI) was 9.78$\times$10$^{5}$ , highest absorption's coefficient among them synthesized by author, and the sensitivity of PVCiA added with PSQD1 (3%) was highly sensitized about 16 times than not added, and higher than NISQ(3%). PSQD1 with substituted 4 and 7 positions by nitrogen is rich in n-$\pi$* transition, resulted in high absorption's coefficient, red shift for another squarylium dyes, and afforded to the highest sensitivity of PVCiA.

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Construction of Dihydro-1,4-dioxins: Synthesis of Dihydro-1,4-dioxin-3-carboxanilides

  • Han, Ho Gyu;Jang, Gi Hyeok;Nam, Gi Dal
    • Bulletin of the Korean Chemical Society
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    • v.22 no.2
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    • pp.149-153
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    • 2001
  • A new methodology for construction of dihydro-1,4-dioxin skeleton was described. Introduction of thio group at the ${\alpha}-position$ of 8 followed by chlorination gave 11, which was to prevent an enolization as well as to promote the facile nucleophilic substitution reaction of ethylene glycol giving 16 in equilibrium with cyclic ether 19. Removal of thio group of 19 and dehydration in the presence of an acid catalyst gave dihydro-1,4-dioxin 21. In case of electron withdrawing trifluoromethyl group is subsituted in C-2, 18 was converted to the corresponding dihydro-1,4-dioxin 20 by the halogenation of hydroxy followed by treatment of triethylamine.

Solvolysis of 1-(4-methoxyphenyl)-1-aryl-2,2,2-trifluoroethyl chlorides

  • 여수동;권정민;변성일;Mizue Fujio;Masaaki Mishima;Yuho Tsuno
    • Bulletin of the Korean Chemical Society
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    • v.17 no.3
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    • pp.228-234
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    • 1996
  • The rates of solvolysis of 1-(4-methoxyphenyl)-1-aryl-2,2,2-trifluoroethyl chlorides[I] in a variety of solvents were measured by an electroconductometric method. LArSR relationships (Yukawa-Tsuno eq.)were found to give a linear plot, log(k/ko)=-1.84[σo+0.918(σ+-σo)], in 80% aqueous ethanol. Small |ρ| and r values in comparison with 1-aryl-1-(trifluoromethyl)ethyl tosylate(ρ=-6.09, r=1.59) suggested that the carbocationic charge in the transition state was dispersed by a strong p-π donor, p-methoxy group. Linear mY plots with m 0.90 for all of the substituents in aqueous acetone and m=0.60-0.82 for those of aqueous ethanol indicate that this solvolysis proceeds via an SN1 mechanism with nucleophilic solvent assistance. Thiourea effects and isokinetic temperatures for the rate of solvolysis also can prove the above mechanism.

An Effective Acylation of Cephalosporins Using 1-Methanesulfonyloxy-6-trifluoromethylbenzotriazole$^\dag$

  • Lee, Cheol-Hae;Moon, Chi-Jang;Kim, Kyeong-Sook;Kim, Jae-Hak;Kim, Dae-Whang
    • Bulletin of the Korean Chemical Society
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    • v.8 no.4
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    • pp.336-338
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    • 1987
  • A new coupling agent, 1-methanesulfonyloxy-6-trifluoromethyl-benzotriazole (3), was prepared by the reaction of 1-hydroxy-6-trifluoromethylbenzotriazole (1) and methanesulfonyl chloride. 3 was reacted with 2-(2-amino-4-thiazolyl)-2-synalkoxyi minoacetic acid (4) to give a mixture of active intermediates (5 and 6), which was treated with 7-aminocephalosporanic acid derivatives (10) to afford cephalosporin derivatives (11) in short reaction time with high yields.

Residual Stress Behavior of PMDA/6FDA-PDA Copolyimide Thin Films (PMDA/6FDA-PDA 공중합 폴리이미드의 잔류응력 거동)

  • Jang, Won Bong;Chung, Hyun Soo;Joe, Yungil;Han, Haksoo
    • Applied Chemistry for Engineering
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    • v.10 no.7
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    • pp.1014-1019
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    • 1999
  • Copolyamic acid PMDA/6FDA-PDA(PAA) and homopolyamic acids PMDA-PDA(PAA) and 6FDA-PDA(PAA) were synthesized from 1,2,4,5-benzenetetracarboxylic dianhydride(PMDA) and 2,2'-bis(3,4-dicarboxyphenyl) hexafluoropropane dianhydride(6FDA) as the dianhydride and 1,4-phenylenediamine (PDA) as the diamine. Residual stresses were detected in-situ during thermal imidization of the co- and homopolyimide precursors as a function of processing temperature over the range of $25{\sim}400^{\circ}C$ using thin film stress analyzer(TFSA), and morphological structures were investigated by WAXD. In comparison, the resultant residual stress of polyimide films composed of different compositions decreased with the increasing content of PMDA unit in the chain and was about 5 Mpa in compression mode for PMDA-PDA. In this study, the synthesis of random PMDA/6FDA-PDA copolyimide could be completed and compensate for the difficulty of process due to high $T_g$ of PMDA-PDA and relatively higher stress of 6FDA-PDA. It showed that we can make a low level stress copolyimied having excellent mechanical properties by incorporating appropriate rod-like rigid structure PMDA-PDA unit into 6FDA-PDA polyimide backbone which generally shows higher stress due to rotational hinges such as bulky di(trifluoromethyl). Specially, PMDA/6FDA-PDA(0.9:0.1:1.0) satisfied excellent mechanical property and low level stress as an inter layer showing low dielectric constant.

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Residual Characteristics of a Systemic Insecticide Flonicamid and Its Metabolites in Sweet Pepper (착색단고추 중 침투성농약 플로니카미드 및 대사물질의 생성 및 잔류양상)

  • Seo, Eun-Kyung;Kim, Taek-Kyum;Hong, Su-Myeong;Kwon, Hye-Young;Gwon, Ji-Hyeong;Cho, Nam-Jun
    • The Korean Journal of Pesticide Science
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    • v.18 no.4
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    • pp.228-235
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    • 2014
  • The residue levels of flonicamid and its metabolites, 4-(trifluoromethyl)nicotinic acid (TFNA) and N-4-(trifluoromethyl)nicotinoyl glycine (TFNG) in sweer pepper were investigated to examine the residual characteristics of analytes for 87 days after pesticide application. The pesticide was applied once at recommended dosage and double dosage by foliar sprays and the samples of fruits and leaves of sweet pepper were collected for each treatment. The residues of flonicamid in all of fruits and leaves decreased gradually over time, while the residue levels of TFNG metabolite exhibited tendency that increased for long periods and thereafter decreased. Total flonicamid residual concentrations containing metabolites residues in fruit samples increased consistently until 30 days post-application and higher residue levels than residues at 1 day post-application were detected from 30 day to 87 day after treatment. The residue pattern observed in fruit could be explained by the movement of TFNG from leaves to fruits of plant. Such residual characteristic was similarly found in samples treated both recommended dosage and double dosage.

Residual Stress Behavior and Physical Properties of Colorless and Transparent Polyimide Films (무색 투명 폴리이미드 박막의 잔류응력 거동 및 특성분석)

  • Nam, Ki-Ho;Lee, Wansoo;Seo, Kwangwon;Han, Haksoo
    • Polymer(Korea)
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    • v.38 no.4
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    • pp.510-517
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    • 2014
  • A series of polyimide (PI) was prepared by reacting 4,4'-(hexafluoroisopropylidene)-diphthalic anhydride (6FDA) as the anhydride and bis(3-aminophenyl) sulfone (APS), bis[4-(3-aminophenoxy)-phenyl] sulfone (BAPS), 2,2-bis(4-aminophenyl)-hexafluoropropane (6FPD), 2,2-bis[4-(4-aminophenoxy)-phenyl]hexafluoropropane (6FBAPP), 2,2'-bis(trifluoromethyl)benzidine (TFDB), or 1,4-phenylenediamine (PDA) as the diamine. Residual stress behaviors were detected in-situ during thermal imidization of the polyimide precursors using a thin film stress analyzer (TFSA), and interpreted with respect to their morphology. According to the molecular orientation and packing order, the residual stress varied from 23.1 to 12.5 MPa, decreased with increasing chain rigidity. The thermal properties of the PI films were investigated using differential scanning calorimetry (DSC), thermogravimetric analysis (TGA), and thermomechanical analysis (TMA). Their optical properties were measured by ultraviolet-visible spectrophotometer (UV-vis), and spectrophotometry. The properties of PI films were found to be strongly dependent upon the morphological structure. However, trade-offs between residual stress and optical properties were identified.