Identification of benzofuran central cores for the inhibition of leukotriene A4 hydrolase

Eccles, Wendy; Blevitt, Jonathan M.; Booker, Jamila N.; Chrovian, Christa C.; Crawford, Shelby; Leon, Aimee Rose de; Deng, Xiaohu; Fourie, Anne M.; Grice, Cheryl A.; Herman, Krystal; Karlsson, Lars; Kearney, Aaron M.; Lee-Dutra, Alice; Liang, Jimmy T.; Luna, Rosa; Pippel, Dan; Rao, Navin; Riley, Jason P.; Santillán, Alejandro; Savall, Brad M.; Tanis, Virginia M.; Xue, Xiaohua; Young, Arlene L.

doi:10.1016/j.bmcl.2012.11.074

Cited by 13 publications

(8 citation statements)

References 6 publications

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“…IR: 3265, 1691IR: 3265, , 1657IR: 3265, , 1596IR: 3265, , 1555IR: 3265, , 1498 . 1 H NMR (400 MHz, DMSO-d 6 ): δ = 2.17-2.28 (m, 1 H, CH 2 CH 2 CH), 2.48-2.62 (m, 2 H, CH 2 CH 2 CH), 2.66-2.78 (m, 1 H, CH 2 CH 2 CH), 4.42 (dd, J = 15.2, 6.0 Hz, 1 H, NHCH 2 ), 4.49 (dd, J = 15.2, 6.0 Hz, 1 H, NHCH 2 ), 4.68 (m, 1 H, CH 2 CH 2 CH), 6.25 (t, J = 6.0 Hz, 1 H, CH 2 NH), 6.99 (dd, J = 7.6, 1.6 Hz, 1 H, ArH), 7.10 (td, J = 7.6, 1.6 Hz, 1 H, ArH), 7.14-7.21 (m, 2 H, ArH), 7.30 (m, 3 H, ArH), 7.45 (d,J = 7.9 Hz,2 H,ArH). ,5.21;N,8.52.…”

Section: -Oxo-1-phenylpyrrolidine-2-carboxylic Acid 2-chlorobenzylammentioning

confidence: 99%

“…1 H NMR (400 MHz, CDCl 3 ): δ = 2.12-2.32 (m, 2 H, CH 2 CH 2 CH), 2.47-2.57 (m, 1 H, CH 2 CH 2 CH), 2.71-2.84 (m, 1 H, CH 2 CH 2 CH), 3.34 (s, 3 H, OCH 3 ), 5.32 (dd, J = 5.9, 1.2 Hz, 1 H, CH 2 CH 2 CH), 7.20 (t, J = 2.0 Hz, 1 H, ArH), 7.55 (d,J = 2.0 Hz,2 H,ArH). Anal.…”

Section: N-(35-dichlorophenyl)-5-methoxypyrrolidin-2-one (42)mentioning

confidence: 99%

“…Yield: 0.5 mmol (25%); white solid (EtOAc/n-heptane, 1:1); mp 107-108 °C (EtOAc/n-heptane); R f = 0.39 (EtOAc/n-heptane, 6:4). IR: 3368, 1713IR: 3368, , 1585IR: 3368, , 1562IR: 3368, , 1513IR: 3368, , 1445IR: 3368, , 1370IR: 3368, , 1204 (d, J = 8.3 Hz, 1 H, NH), 5.63 (sym m, 1 H, CH 2 CH 2 CH), 6.64 (d,J = 7.8 Hz,1 H,ArH),2 H,ArH),1 H,ArH), 7.13 (d, J = 1.9 Hz, 1 H, ArH), 7.48 (d, J = 1.9 Hz, 2 H, ArH). Anal.…”

Section: N-(35-dichlorophenyl)-5-methoxypyrrolidin-2-one (42)mentioning

confidence: 99%

“…46 Yield: 0.26 mmol (26%). 1 H NMR (400 MHz, CDCl 3 ): δ = 4.02 (s, 6 H, 2OCH 3 ), 7.01 (t, J = 8.2 Hz, 2 H, ArH), 7.07 (d,J = 8.2 Hz,2 H,ArH), 7. 2 H,ArH), 7.62-7.66 (m, 2 H, ArH).…”

Section: N-(35-dichlorophenyl)-5-methoxypyrrolidin-2-one (42)mentioning

confidence: 99%

See 3 more Smart Citations

Impact of Functional Groups on the Copper-Initiated N-Arylation of 5-Functionalized Pyrrolidin-2-ones and Their Vinylogues

et al. 2016

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Section: -Oxo-1-phenylpyrrolidine-2-carboxylic Acid 2-chlorobenzylammentioning

confidence: 99%

Section: N-(35-dichlorophenyl)-5-methoxypyrrolidin-2-one (42)mentioning

confidence: 99%

Section: N-(35-dichlorophenyl)-5-methoxypyrrolidin-2-one (42)mentioning

confidence: 99%

“…46 Yield: 0.26 mmol (26%). 1 H NMR (400 MHz, CDCl 3 ): δ = 4.02 (s, 6 H, 2OCH 3 ), 7.01 (t, J = 8.2 Hz, 2 H, ArH), 7.07 (d,J = 8.2 Hz,2 H,ArH), 7. 2 H,ArH), 7.62-7.66 (m, 2 H, ArH).…”

Section: N-(35-dichlorophenyl)-5-methoxypyrrolidin-2-one (42)mentioning

confidence: 99%

See 2 more Smart Citations

Impact of Functional Groups on the Copper-Initiated N-Arylation of 5-Functionalized Pyrrolidin-2-ones and Their Vinylogues

et al. 2016

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“…3-Hydroxymethylbenzofuran, an important intermediate of active benzofuran derivatives [5][6][7][8], is usually synthesized by the reduction of benzofuran-3-carbaldehyde with NaBH 4 [9,10]. In this paper, we report a new method for the synthesis of 3-hydroxymethylbenzofuran.…”

Section: Introductionmentioning

confidence: 99%

A new method for the synthesis of 3-hydroxymethylbenzofuran

Luo

Liu

Zhang

et al. 2013

Chinese Chemical Letters

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Discussion Addendum for: Convenient Preparation of 3‐Ethoxycarbonyl Benzofurans from Salicylaldehydes and Ethyl Diazoacetate

Rahaman

Hossain

2020

Organic Syntheses

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The benzofuran scaffold is an important heterocyclic core component found in several natural products and in polymers. Typically, 2,3‐disubstituted benzofurans are notable building blocks in many medicinal and biologically active compounds. In addition, 3‐substituted benzofurans act as anticancer agents, antitubercular agents, antimicrobial agents, antiviral agents, and anti‐inflammatory agents. This addendum discusses the preparation of 3‐ethoxycarbonyl benzofurans from salicylaldehydes and ethyl diazoacetate. It presents alternate methods to prepare 3‐alkoxycarbonyl benzofurans through four schemes: synthesis by a thallium catalyzed oxidation annulation, synthesis by a palladium‐catalyzed cyclization, synthesis by a palladium assisted CO insertion, and synthesis by a copper‐catalyzed cyclization. The addendum also provides information on the applications of the one‐pot synthetic method that has been used by the authors and by other groups in the preparation of several biologically active compounds in organic synthesis.

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Identification of benzofuran central cores for the inhibition of leukotriene A4 hydrolase

Cited by 13 publications

References 6 publications

Impact of Functional Groups on the Copper-Initiated N-Arylation of 5-Functionalized Pyrrolidin-2-ones and Their Vinylogues

Impact of Functional Groups on the Copper-Initiated N-Arylation of 5-Functionalized Pyrrolidin-2-ones and Their Vinylogues

A new method for the synthesis of 3-hydroxymethylbenzofuran

Discussion Addendum for: Convenient Preparation of 3‐Ethoxycarbonyl Benzofurans from Salicylaldehydes and Ethyl Diazoacetate

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