2,7-Bis-<i>N</i>,<i>N</i>-dimethylaminochalcogenoxanthen-9-ones via Electrophilic Cyclization with Phosphorus Oxychloride

Valle, David J. Del; Donnelly, David J.; Holt, Jason J.; Detty, Michael R.

doi:10.1021/om050225o

Cited by 36 publications

(36 citation statements)

References 9 publications

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“…19,20 Compound 14 replaces a dimethylamino substituent with an azadecalin substituent. The fused aniline equivalent of this substitution is known as julolidine (Chart 2) and compounds derived from 14 are referred to as “julolidyl” rhodamines in the remainder of the manuscript.…”

Section: Resultsmentioning

confidence: 99%

“…Directed ortho -lithiation of 20 in THF at −78 °C with sec -butyllithium and N,N,N’,N’ -tetramethylethylenediamine (TMEDA) was followed immediately by the addition of 3-dimethylaminophenyl disulfide ( 21 ) 19,23 at −78 °C to minimize the amount of self-condensed side product formation that has been seen in similar reactions. The isolated yield of diaryl sulfide 22 was 35-45%.…”

Section: Resultsmentioning

confidence: 99%

“…The isolated yield of diaryl sulfide 22 was 35-45%. Subsequent cyclization of 22 with POCl 3 in acetonitrile 19 gave the desired thioxanthone 15 in 90-91% isolated yield, putting the overall yield for the synthesis of the half-julolidyl thioxanthone 15 at 20%.…”

Section: Resultsmentioning

confidence: 99%

“…Trifluoroacetic anhydride was added to CH 2 Cl 2 solutions of thioamides 2, 4, 6, 8, 10 and 12 to give the corresponding amides in isolated yields of 51-70%. 19 …”

Section: Resultsmentioning

confidence: 99%

“…Thiorhodamines 4 15 and 8 15 and thioxanthones 13 19 and 14 20 were prepared by literature methods. Reactions were run under argon.…”

Section: Methodsmentioning

confidence: 99%

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Thiorhodamines containing amide and thioamide functionality as inhibitors of the ATP-binding cassette drug transporter P-glycoprotein (ABCB1)

Orchard¹,

Schamerhorn²,

Calitree³

et al. 2012

Bioorganic & Medicinal Chemistry

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Twelve thiorhodamine derivatives have been examined for their ability to stimulate the ATPase activity of purified human P-glycoprotein (P-gp)-His10, to promote uptake of calcein AM and vinblastine into multidrug-resistant, P-gp-overexpressing MDCKII-MDR1 cells, and for their rates of transport in monolayers of multidrug-resistant, P-gp-overexpressing MDCKII-MDR1 cells. The thiorhodamine derivatives have structural diversity from amide and thioamide functionality (N,N-diethyl and N-piperidyl) at the 5-position of a 2-thienyl substituent on the thiorhodamine core and from diversity at the 3-amino substituent with N,N-dimethylamino, fused azadecalin (julolidyl), and fused N-methylcyclohexylamine (half-julolidyl) substituents. The julolidyl and half-julolidyl derivatives were more effective inhibitors of P-gp than the dimethylamino analogues. Amide-containing derivatives were transported much more rapidly than thioamide-containing derivatives.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

“…Trifluoroacetic anhydride was added to CH 2 Cl 2 solutions of thioamides 2, 4, 6, 8, 10 and 12 to give the corresponding amides in isolated yields of 51-70%. 19 …”

Section: Resultsmentioning

confidence: 99%

“…Thiorhodamines 4 15 and 8 15 and thioxanthones 13 19 and 14 20 were prepared by literature methods. Reactions were run under argon.…”

Section: Methodsmentioning

confidence: 99%

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Thiorhodamines containing amide and thioamide functionality as inhibitors of the ATP-binding cassette drug transporter P-glycoprotein (ABCB1)

Orchard¹,

Schamerhorn²,

Calitree³

et al. 2012

Bioorganic & Medicinal Chemistry

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Selenium and Tellurium Heterocycles

Logan

Lang

Detty

2014

Patai's Chemistry of Functional Groups

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Synthetic pathways leading to tellurium‐ and selenium‐containing heterocycles are summarized for the period 1995 to the present. In addition, the utility of various tellurium‐ and selenium‐containing heterocycles are summarized. Primarily, the synthesis of tellurium‐ and selenium‐containing heterocycles of five‐ and six‐membered rings are described with various degrees of unsaturation, as well as their benzo‐fused analogues. In particular, the syntheses of selenophenes , tellurophenes and their mono‐ and dibenzo‐fused analogues are described. Similarly, syntheses of tellurazoles, selenazoles, telluradiazoles, selenadiazoles and their benzo‐fused analogues are described. Among the six‐membered rings, synthetic routes to telluropyrans and selenopyrans and their benzo analogues are described. Further degrees of unsaturation provide the telluropyrylium and selenopyrylium compounds and their benzo‐ and dibenzo‐fused analogues. Synthetic routes to chalcogenopyrylium compounds, chalcogenorosamine compounds and chalcogenorhodamine compounds are described and some of the uses of these materials are also provided. A review of synthetic routes to the core‐modified porphyrins—21‐chalcogenoporphyrins and 21,23‐dichalcogenoporphyrins—is also provided. Porphyrin‐like molecules with an expanded structure of five or six‐membered rings in the porphyrin core are also reviewed.

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An Optochemical Oxygen Scavenger Enabling Spatiotemporal Control of Hypoxia

et al. 2023

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We present an optochemical O2 scavenging system that enables precise spatiotemporal control of the level of hypoxia in living cells simply by adjusting the light intensity in the illuminated region. The system employs rhodamine containing a selenium or tellurium atom as an optochemical oxygen scavenger that rapidly consumes O2 by photochemical reaction with glutathione as a coreductant upon visible light irradiation (560–590 nm) and has a rapid response time, within a few minutes. The glutathione‐consuming quantum yields of the system were calculated as about 5 %. The spatiotemporal O2 consuming in cultured cells was visualized with a hypoxia‐responsive fluorescence probe, MAR. Phosphorescence lifetime imaging was applied to confirmed that different light intensities could generate different levels of hypoxia. To illustrate the potential utility of this system for hypoxia research, we show that it can spatiotemporally control calcium ion (Ca2+) influx into HEK293T cells expressing the hypoxia‐responsive Ca2+ channel TRPA1.

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2,7-Bis-N,N-dimethylaminochalcogenoxanthen-9-ones via Electrophilic Cyclization with Phosphorus Oxychloride

Cited by 36 publications

References 9 publications

Thiorhodamines containing amide and thioamide functionality as inhibitors of the ATP-binding cassette drug transporter P-glycoprotein (ABCB1)

Thiorhodamines containing amide and thioamide functionality as inhibitors of the ATP-binding cassette drug transporter P-glycoprotein (ABCB1)

Selenium and Tellurium Heterocycles

An Optochemical Oxygen Scavenger Enabling Spatiotemporal Control of Hypoxia

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