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6. Synthesis of Novel 8‐cyclo‐1,5,3,7‐Diazadiphosphocine Derivatives Via [4 + 2] Cycloaddition.

Author

Bae, Song Mi, Chen, Yu, Jeong, Il Soo, Cho, Jong Hyun, Song, Ju Hyun, and Jung, Dai Il

Subjects
TRANSITION metal ions, CHELATING agents, RING formation (Chemistry), PHOSPHINIC acid, CHELATES, ISOXAZOLIDINES, DIENOPHILES
Abstract

As part of our research program into pharmacologically valuable compounds and chelating agents for transition metal ions, novel 8‐cyclo‐1,5,3,7‐diazadiphosphocines (5–16) were successfully synthesized in good yields via [4 + 2] cycloaddition reaction between 8‐cyclo‐1,5,3,7‐diazadiphosphocines (4a‐c) with dienophiles (dimethyl acetylenedicarboxylate [DMAD], diethyl acetylenedicarboxylate [DEAD], diethyl diazene‐1,2‐dicarboxylate [DEDAD], and diisopropyl diazene‐1,2‐dicarboxylate [DIPDAD]). The core precursor scaffolds (4a‐c) were prepared via a one‐pot reaction between heteroaromatic amine analogs (1a‐c), paraformaldehyde and hypophosphorous acid in the presence of 6 M HCl. The biological activity of all synthesized 8‐cyclo‐1,5,3,7‐diazadiphosphocines (4a‐c, and 5–16) was evaluated against several cancer cell lines. [ABSTRACT FROM AUTHOR]

Published
2021
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7. Synthesis of Novel 8‐cyclo‐1,5,3,7‐DiazadiphosphocineDerivatives Via [4 + 2] Cycloaddition

Author

Bae, Song Mi, Chen, Yu, Jeong, Il Soo, Cho, Jong Hyun, Song, Ju Hyun, and Jung, Dai Il

Abstract

As part of our research program into pharmacologically valuable compounds and chelating agents for transition metal ions, novel 8‐cyclo‐1,5,3,7‐diazadiphosphocines (5–16) were successfully synthesized in good yields via [4 + 2] cycloaddition reaction between 8‐cyclo‐1,5,3,7‐diazadiphosphocines (4a‐c) with dienophiles (dimethyl acetylenedicarboxylate [DMAD], diethyl acetylenedicarboxylate [DEAD], diethyl diazene‐1,2‐dicarboxylate [DEDAD], and diisopropyl diazene‐1,2‐dicarboxylate [DIPDAD]). The core precursor scaffolds (4a‐c) were prepared via a one‐pot reaction between heteroaromatic amine analogs (1a‐c), paraformaldehyde and hypophosphorous acid in the presence of 6 M HCl. The biological activity of all synthesized 8‐cyclo‐1,5,3,7‐diazadiphosphocines (4a‐c, and 5–16) was evaluated against several cancer cell lines. Cyclic 1,5,3,7‐diazadiphosphocines 4a‐cwere generated via a one‐pot reaction of 1a‐c, respectively, with H3PO2and paraformaldehyde. These dienes were utilized to assemble 12 novel 8‐membered cyclic 1,5,3,7‐diazadiphosphocine derivatives 5–16via [4 + 2] cycloaddition with dienophiles P, Q, S, and T.The cytotoxicity of the new 8‐cyclo‐1,5,3,7‐diazadiphosphines 5–16was evaluated against three cancer cell lines.

Published
2021
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8. A Study on the Reactions of Diamines with 2,5-Dimethoxytetrahydrofuran and 1,3-Acetonedicarboxylic Acid

Author

Lee Do-Hun, Choi Soon-Kyu, Jung Dai-Il, Song Ju-Hyun, Park Yu-Mi, Hahn Jung-Tai, and Lee Yong-Gyun

Subjects
Steric effects, chemistry.chemical_compound, chemistry, Propane, Yield (chemistry), Acetonedicarboxylic acid, chemistry.chemical_element, Organic chemistry, Ethylenediamine, Benzene, Carbon, Medicinal chemistry, Octane
Abstract

In order to synthesize novel anticonvulsants, we researched that the reactions of diamines with 2,5-dimethoxytetrahydrofuran and 1,3-acetonedicarboxylic acid. The reaction of ethylenediamine with 2,5-dimethoxytetrahydrofuran and 1,3-acetonedicarboxylic acid afforded 8-(2-pyrrol-1-yl-ethyl)-8-aza-bicyclo[3,2,1]octan-3-one (yield; 5.0%) and 1,2-di-(8-aza-bicyclo[3,2,1]octan3-onyl)ethane (yield; 17.0%). In case of 1,3-diaminopropane, 8-(3-pyrrol-1-yl-propyl)-8-aza-bicyclo[3,2,1]octan-3-one(yield; 6.0%) and 1,3-di-(8-aza-bicyclo[3,2,1]octan-3-onyl)propane (yield; 21.0%) were obtained. In case of 1,8-diaminooctane, 8-(8-pyrrol-1-yl-octyl)-8-aza-bicyclo-[3,2,1]octan-3-one (yield; 2.6 %) and 1,8-di-(8-aza-bicyclo[3,2,1]octan-3-onyl)octane (yield; 24.9%) were obtained. In diaminobenzene reactions, synthetic yields of 8-aza-bicyclo-[3,2,1]octan-3-one derivatives were higher than those of pyrrole derivatives because re actions were done under room temperature. The longer the carbon chain of diaminoalkane is, the more reactive N atom is due to more electron donating effect, and the less steric hindrance around the carbon gave the higher chemical yields. The reaction of p-phenylenediamine as a diaminobenzene with 2,5-dimethoxyte-trahydrofuran and 1,3-acetonedicarboxylic acid produced p-dipyrrolylbenzene (yield; 4.0%), 8-(4-pyrrol-1-yl-phenyl)-8-aza-bicyclo[3,2,1]octan-3-one (yield; 12.0%), and 1,4-di-(8-aza-bicyclo[3,2,1]octan-3-onyl)benzene (yield; 59.0%). In case of m-phenylenediamine, 8-(3-pyrrol-1-yl-phenyl)-8-aza-bicyclo[3,2,1]octan-3-one(yield; 2.0%) and 1,3-di-(8-aza-bicyclo[3,2,1]octan-3-onyl)benzene (yield ; 28.0%) were obtained. But, synthesis of 1,2-di-(8-aza-bicyclo[3,2,l]octan-3-onyl)benzene by treatment of o-phenylenediamine was not successful, presumably due to the steric hindrance of 8-aza-bicyclo-[3,2,1]octan-3-one rings.

Published
2006

9. Synthesis Of 1,5-Benzodiazepine Derivatives

Author

Jung Dai-Il, Jung Doo-Hee, Kim Yun-Young, Kim In-Shik, Lee Yong-Gyun, Choi Tae-wonchoi, and Park You-Mi

Subjects
chemistry.chemical_compound, Benzodiazepine, chemistry, medicine.drug_class, Organic Chemistry, Acetonedicarboxylic acid, Acetone, medicine, Organic chemistry, Acetophenone
Abstract

2,4,4-Trirnethyl-3H-5-hydro-l,5-benzodiazepine was obtained by the reaction of o-phenylenediamine and acetonedicarboxylic acid (or acetone) in various methods (Method 1, 2, 3). When o-phenylenediamine was heated with acetophenone in the presence of PPA (or SiO2), 2,4-diphenyl-4-methyl-3H-5-hydro-1,5-benzodiazepine 5 was isolated (Method 4).

Published
1999

42. Discovery of Desketoraloxifene Analogues as Inhibitors of Mammalian, Pseudomonas aeruginosa, and NAPE Phospholipase D Enzymes

Author

Scott, Sarah A., Spencer, Cierra T., O’Reilly, Matthew C., Brown, Kyle A., Lavieri, Robert R., Cho, Chul-Hee, Jung, Dai-Il, Larock, Richard C., Brown, H. Alex, and Lindsley, Craig W.

Abstract

Phospholipase D (PLD) hydrolyses cellular lipids to produce the important lipid second messenger phosphatidic acid. A PLD enzyme expressed by Pseudomonas aeruginosa(PldA) has been shown to be important in bacterial infection, and NAPE-PLD has emerged as being key in the synthesis of endocannabinoids. In order to better understand the biology and therapeutic potential of these less explored PLD enzymes, small molecule tools are required. Selective estrogen receptor modulators (SERMs) have been previously shown to inhibit mammalian PLD (PLD1 and PLD2). By targeted screening of a library of SERM analogues, additional parallel synthesis, and evaluation in multiple PLD assays, we discovered a novel desketoraloxifene-based scaffold that inhibited not only the two mammalian PLDs but also structurally divergent PldA and NAPE-PLD. This finding represents an important first step toward the development of small molecules possessing universal inhibition of divergent PLD enzymes to advance the field.

Published
2015
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48. Rhodium-catalyzed tandem conjugate addition-Mannich cyclization reaction: straightforward access to fully substituted tetrahydroquinolines.

Author

Youn SW, Song JH, and Jung DI

Abstract

A new Rh(I)-catalyzed tandem conjugate addition-Mannich cyclization reaction of imine-substituted electron-deficient alkenes with arylboronic acids has been developed to afford 2,3,4-trisubstituted 1,2,3,4-tetrahydroquinolines. This is the first example involving imine group as a secondary electrophile in Rh(I)-catalyzed tandem reactions.

Published
2008
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