Identification of Thiaindans in Crude Oil by Gas-Liquid Chromatography, Desulfurization, and Spectral Techniques.

Thompson, Charles J.; Coleman, H.J.; Hopkins, R.L.; Rall, H.T.

doi:10.1021/ac60243a026

Cited by 16 publications

(6 citation statements)

References 6 publications

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“…An interesting parallel exists between the structures of the benzothiophenes described in this report and those of the 1-TIME, minutes (9). Most of the ring structures present in one exist also in the other and in much the same order of magnitude.…”

Section: Wavelength Micronssupporting

confidence: 60%

Identification of alkylbenzo[b]thiophenes in a Wasson, Texas, crude oil distillate boiling 200 to 250.deg.

Hopkins¹,

Coleman²,

Thompson³

et al. 1969

Anal. Chem.

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Section: Wavelength Micronssupporting

confidence: 60%

Identification of alkylbenzo[b]thiophenes in a Wasson, Texas, crude oil distillate boiling 200 to 250.deg.

Hopkins¹,

Coleman²,

Thompson³

et al. 1969

Anal. Chem.

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“…Alcohol 23 has not been well characterized to date. Thus, we obtained the following data to substantiate the structure; n 26.8 1.5582 [lit …”

Section: Methodsmentioning

confidence: 92%

“…Vacuum distillation (56−58 °C/0.37 mm) gave a pale yellow oil (6.97 g, 80.5%) which was further purified over silica gel (hexanes); n 25.6 1.5757. The compound 24 has not been well characterized, but certain derivatives have been reported . Our spectral data are as follows: 1 H NMR (DCCl 3 ) δ 1.35 [s, 6 H, C(C H 3 ) 2 ], 3.16 [s, 2 H, SC H 2 ], 7.02−722 [m, 4 H, Ar-H]; 13 C NMR (DCCl 3 ) δ 27.2 [C( C H 3 ) 2 ], 46.9 [S C H 2 ], 46.9 [ C (CH 3 ) 2 ], Ar-C [122.0, 122.3, 124.1, 127.0, 140.1, 147.5].…”

Section: Methodsmentioning

confidence: 99%

“…The resulting mixture was stirred for 5 min with gentle warming and 5 min at room temperature. Ether extracts of the resulting mixture were dried (Na 2 SO 4 ) and evaporated to an oil which was vacuum distilled with the main fraction distilling at 80−85 °C/0.12 mm [lit. , 136−137 °C/12 mm]. Chromatography of the oil over silica gel (3:1 hexanes:ether) gave 22 as a yellow oil (5.6 g, 56%).…”

Section: Methodsmentioning

confidence: 99%

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Biologically Active Heteroarotinoids Exhibiting Anticancer Activity and Decreased Toxicity

et al. 1997

J. Med. Chem.

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A series of retinoids, containing heteroatoms in a cyclic ring and called heteroarotinoids, were synthesized, and their biological activity was evaluated using tissue culture lines that have measurable responses to trans-retinoic acid (t-RA). Transglutaminase (TGase) was assessed in the human erythroleukemia cell line (GMO6141A) as an indicator of differentiation and apoptosis. Proliferation was evaluated in a human cervical cell line, CC-1, which exhibits dose-dependent alterations in growth rate in response to treatment with trans-retinoic acid. Activation of nuclear retinoic acid receptors was determined in a reporter cell line established from CC-1. The reporter line, called CC-B, contains a reporter gene controlled by a retinoic acid responsive element (RARE) and a thymidine kinase (tk) promoter. Treatment of the CC-B line with the heteroarotinoids resulted in a dose-responsive and retinoid-dependent regulation of reporter gene expression. The heteroarotinoids exhibited activity in all assays and correlated in a statistically significant manner between assays. RARE transactivation activity in CC-B cells correlated with induction of TGase in GMO6141A (R = 0.96) and with a decrease in the growth rate of CC-1 cells (R = -0.90). The ability of the selected heteroarotinoids to induce differentiation, inhibit proliferation, and activate nuclear receptors demonstrates the chemotherapeutic potential of these agents. In view of the biological activity cited, an in vivo toxicity study was conducted on male B6D2F1 mice with three heteroarotinoids, namely 8 [(2E,4E,6E)-3,7-dimethyl-7-(1,2,3,4-tetrahydro-4,4-dimeth ylthiochroman-6-yl)-2,4,6-heptatrienoic acid], 10 [(2E,4E,6E)-3,7-dimethyl-7-(1,2,3,4-tetrahydro-4,4-dimeth ylchroman-6-yl)-2, 4,6-heptatrienoic acid], and 13 [(E)-p-[2-(4,4-dimethylchroman-6-yl)propenyl]benzoic acid]. The mice were used with gavage of heteroarotinoids in corn oil [0.1, 0.2, 0.4, or 0.8 mg/kg] and with 0.01 or 0.05 mg/kg of TTNPB (5) [(E)-4-[2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-1- propenyl]benzoic acid] as reference controls. The target organs affected in the mice by the three heteroarotinoids were those typically associated with t-RA (1) toxicity. The maximum tolerated dose (MTD) of 13 was 9.4 mg/kg/day, which was equal in toxicity to that of t-RA (1) and 1000-fold less toxic than TTNPB (5). The MTDs of 8 and 10 were 34 and 32 mg/kg/day, respectively, which is 3-fold less toxic than t-RA (1) and 3000-fold less toxic than TTNPB (5). The 3000-fold reduced toxicity, compared with only a 27% reduction biological activity of 8 and 10 with respect to that of TTNPB, observed in our assays indicates a good therapeutic ratio of these heteroarotinoids over the parent compound. The biological activity and reduced toxicity of these heteroartinoids demonstrate the potential efficacy as anticancer agents.

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“…Their place is taken, in distillates boiling up to 250 0 C, by thiacydoalkanes [120,124,125], bi-and tricyclothia-alkanes [120], and thiophenes [126]. These molecular types are supplanted in turn by benzothiophenes [119,120] and their variants which include the thiaindanes [127], thienothiophenes [128], dibenzo-and naphthobenzothiophenes and naphthothiophenes [120].…”

Section: Sulfur Compoundsmentioning

confidence: 99%

Crude Petroleum

Speers

Whitehead

1969

Organic Geochemistry

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Identification of Thiaindans in Crude Oil by Gas-Liquid Chromatography, Desulfurization, and Spectral Techniques.

Cited by 16 publications

References 6 publications

Identification of alkylbenzo[b]thiophenes in a Wasson, Texas, crude oil distillate boiling 200 to 250.deg.

Identification of alkylbenzo[b]thiophenes in a Wasson, Texas, crude oil distillate boiling 200 to 250.deg.

Biologically Active Heteroarotinoids Exhibiting Anticancer Activity and Decreased Toxicity

Crude Petroleum

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