Synthesis and characterization of soluble polyimides from 2,2-bis(4-aminophenyl)cycloalkane derivatives

Yi, Mi Hie; Huang, Wenxi; Lee, Bum Jin; Choi, Kil‐Yeong

doi:10.1002/(sici)1099-0518(19990901)37:17<3449::aid-pola2>3.0.co;2-n

Cited by 24 publications

(21 citation statements)

References 5 publications

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“…Materials 2,2-DPANH 2 [16] and 2,2-DPAONH 2 [17] were synthesized according to a procedure reported elsewhere. 1,3-DPANH 2 [18], 1,3-DPAONH 2 [19], 1,3-DPA/OH/NH 2 (unpublished data) and DPA (unpublished data) were prepared according to our previous methods.…”

Section: Methodsmentioning

confidence: 91%

In vitro and in vivo growth inhibition and G1 arrest in human cancer cell lines by diaminophenyladamantane derivatives

Wang¹,

Chen²,

Chi³

et al. 2004

Anti-Cancer Drugs

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We describe the discovery of a novel series of anticancer adamantane derivatives which induce G1 arrest in Colo 205 and HT 29 colon cancer cells. Seven adamantane derivatives were screened for their activity in vitro against 60 human cancer cell lines in the National Cancer Institute (NCI)'s Anticancer Drug Screen system. The relationships between structure and in vitro anticancer activity are discussed. 1,3-Bis(4-(4-amino-3-hydroxyphenoxy)phenyl)adamantane (1,3-DPA/OH/NH2) and 2,2-bis(4-(4-amino-3-hydroxyphenoxy)phenyl)adamantane (DPA) exhibited strong growth inhibitory on anticancer activities in vitro. The IC50s of 1,3-DPA/OH/NH2 (NSC-706835) and DPA (NSC-706832) were found to be < 3 microM against 45 (85%) and 48 (91%) cell lines, respectively. 2,2-Substituted adamantane derivatives exhibited stronger growth inhibition on anticancer activities in vitro than the corresponding 1,3-substituted analogs. Very strong growth inhibition of 2,2-bis(4-aminophenyl)adamantane (NSC-711117) was observed against two colon cancer lines (HT-29 and KM-12), one CNS cancer line (SF-295) and one breast cancer line (NCI/ADR-RES) with IC50 < 1.0 microM, i.e. 0.1, 0.01, 0.059 and 0.079 microM, respectively. In addition, we also examined the in vitro and in vivo effects of DPA on three human colon cancer cells. DPA-treated Colo 205 and HT-29 cells were arrested at G0/G1 as analyzed by flow cytometric analysis. The DPA-induced cell growth inhibition was irreversible after removal of DPA. The in vivo effect of tumor growth suppression by DPA was also observed on colon Colo 205 xenografts. No acute toxicity was observed after an i.p. challenge of DPA in ICR nude mice weekly. These results suggest that DPA appears to be a new potentially less toxic modality of cancer therapy.

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Section: Methodsmentioning

confidence: 91%

In vitro and in vivo growth inhibition and G1 arrest in human cancer cell lines by diaminophenyladamantane derivatives

Wang¹,

Chen²,

Chi³

et al. 2004

Anti-Cancer Drugs

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“…Considerable research efforts have been focused on the synthesis of soluble polyimides that maintain the excellent properties of this class of compounds 4. Typical approaches include the introduction of bulky lateral groups,5–12 flexible linkages,13, 14 kinked15–20 or unsymmetrical structures21, 22 into the polymer backbone.…”

Section: Introductionmentioning

confidence: 99%

Effect of a closure device on complication rates in high‐local‐risk patients: Results of a randomized multicenter trial

Chevalier

Lancelin

Köning

et al. 2003

Cathet Cardio Intervent

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Clinical trials have shown that coronary stenting is associated with a high level of complications at the access site. Arterial sealing devices have proven their efficacy in obtaining immediate hemostasis after sheath removal, in allowing early ambulation, and in improving patient comfort. However, there is no report showing a reduction of local complications related to their use. The purpose of this multicenter study was to compare randomly the efficacy of Angio-Seal versus compression methods of hemostasis in reducing the rate of access site complications after coronary angioplasty in 612 selected patients with higher risk of local events satisfying at least one of the following high-risk criteria: age> 70, previous puncture at the same site, history of hypertension, treatment with ticlopidine at least 2 days before the procedure, use of abciximab, 8 Fr access, prolonged heparin treatment after the angioplasty, and use of lytics if fibrinogen > 1 g/l. Group A (n = 306) had immediate sheath removal, Angio-Seal implantation, and cessation of bed rest 4 hr after the intervention. Group B (n = 306) had sheath removal according to local practice and cessation of bed rest 6-18 hr after the hemostasis procedure, also according to local practice. Clinical follow-up was done at 1 hr, 4 hr, 24 hr, discharge, and 7 days and a systematic color flow duplex sonography was performed to confirm diagnosis of access site complication. In group A, device deployment and immediate hemostasis were obtained in, respectively, 96.8% and 87% of patients. Time to hemostasis was shorter in group A: 5 vs. 52 min (P < 0.001). Cessation of bed rest was dramatically reduced in group A (438 +/- 450 min) vs. group B (952 +/- 308 min; P < 0.001). The cumulative rate of complications, using a composite primary endpoint, at 7 days was significantly different between the two groups: 5.9% of group A patients and 18% of group B patients (P < 0.001). This difference was mainly due to the dramatic reduction of prolonged bleeding in group A patients. Angio-Seal device use in high-local-risk patients allows immediate sheath removal and hemostasis with a reduction of local event rate despite a higher level of anticoagulation, compared to regular compression techniques, directly related to a dramatic decrease of prolonged bleeding.

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“…Raising continuously the molar ratio of BAAD/ODA to 10/0, the integrated films were not available. The reason is that the bulky adamantane groups restricted the growth of the molecular weight of PI . The as‐prepared PI films were characterized by FTIR spectrometry, and the results are shown in Figure .…”

Section: Resultsmentioning

confidence: 99%

“…BAAD was synthesized through the reaction of 2‐adamantanone and aminobenzene according to literature . The details are shown in Scheme S1.…”

Section: Methodsmentioning

confidence: 99%

Synthesis and properties of ultralow dielectric porous polyimide films containing adamantane

Zhou

Dai

et al. 2017

J. Polym. Sci. Part A: Polym. Chem.

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A series of novel ultralow dielectric porous polyimide (PI) films containing adamantane groups was prepared via the thermolysis of polyethylene glycol (PEG) oligomers mixed into PI matrix. Scanning electron microscopy results indicated that the porous PI films showed closed pores with an average diameter of 120 ± 10 nm. Good thermal properties with 5% weight loss temperature of 499 °C in air atmosphere and glass transition temperature in excess of 310 °C were shown for porous PI films. Notably, the ultralow dielectric constant of porous PI films with 1.85 at 1 MHz was obtained and revealed via broadband dielectric spectroscopy. The effects of the chemical structure of the PI matrix and PEG content on the decomposition behavior of PEG and the performance of porous films were investigated. Wide‐angle X‐ray diffraction results indicated that the PI matrix with large d‐spacing generated weaker interactions between the PEG and PI backbone than those of PI matrix with small d‐spacing. As a result, the PEG for the PI matrix with large d‐spacing was completely decomposed. As indicated by the broadband dielectric spectroscopy results, lower dielectric porous PI films were prepared when the PEG contents in the PI matrix increased from 0 to 20 wt %. © 2017 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2018, 56, 549–559

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Synthesis and characterization of soluble polyimides from 2,2-bis(4-aminophenyl)cycloalkane derivatives

Cited by 24 publications

References 5 publications

In vitro and in vivo growth inhibition and G1 arrest in human cancer cell lines by diaminophenyladamantane derivatives

In vitro and in vivo growth inhibition and G1 arrest in human cancer cell lines by diaminophenyladamantane derivatives

Effect of a closure device on complication rates in high‐local‐risk patients: Results of a randomized multicenter trial

Synthesis and properties of ultralow dielectric porous polyimide films containing adamantane

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