Search

Your search keyword '"Davulcu, Akin H."' showing total 22 results
Start Over Author "Davulcu, Akin H."
22 results on '"Davulcu, Akin H."'

1. Indole diterpene synthesis studies: Development of a second-generation synthetic strategy for ()-nodulisporic acids A and

Author

Smith, Amos B., III, Kurti, Laszlo, Davulcu, Akin H., Young Shin Cho, and Ohmoto, Kazuyuki

Subjects
Indole -- Chemical properties, Ring formation (Chemistry) -- Analysis, Acids -- Chemical properties, Biological sciences, Chemistry
Abstract

A second-generation strategy is described for constructing of ()-nodulisporic acid A and B, which is based on the development of a new, effective modular indole synthesis by using a sequential Stille cross-coupling/Buchwald-Hartwig union/cyclization tactic. This method is developed due to considerable acid instability of the C(24) hydroxyl group seen in many advanced intermediates during the first-generation approach.

Published
2007

2. Indole diterpene synthesis studies. Total synthesis of ()-nodulisporic acid F and C construction of the heptacyclic cores of ()-nodulisporic acids A and B and (-)-nodulisporic acid D

Author

Smith, Amos B., III, Davulcu, Akin H., Young Shin Cho, Ohmoto, Kazuyuki, Kurti, Laszlo, and Ishiyama, Haruaki

Subjects
Indole -- Chemical properties, Organic acids -- Chemical properties, Chemistry, Analytic, Biological sciences, Chemistry
Abstract

A first-generation strategy is described for the construction of ()-nodulisporic acids A and B. The preparation of heptacyclic core of ()-nodulisporic acids A and B, the total synthesis of ()-nodulisporic acid F and elaboration of the heptacyclic core of (-)-nodulisporic acid D are achieved.

Published
2007

3. Process research and development for a tetrazole-based growth hormone secretagogue (GHS) pharmaceutical development candidate

Author

Davulcu, Akin H., McLeod, Douglas D., Jun Li, Katipally, Kishta, Littke, Adam, Doubleday, Wendel, Zhongmin Xu, McConlogue, Cary W., Chaijen J. Lai, Gleeson, Margaret, Schwinden, Mark, and Parsons, Rodney L., Jr.

Subjects
Crystalline polymers -- Chemical properties, Crystalline polymers -- Structure, Heterocyclic compounds -- Chemical properties, Heterocyclic compounds -- Structure, Phosphates -- Chemical properties, Phosphates -- Structure, Biological sciences, Chemistry
Abstract

The process research and development efforts that have enabled the synthesis of the phosphate salt of BMS-317180 on a multi-kilogram scale are described. The development of the process has focused on safe execution and the requirement for telescoped synthetic transformations to contend with a lack of suitably crystalline products.

Published
2009

4. Discovery of Potent and Orally Bioavailable Dihydropyrazole GPR40 Agonists

Author

Shi, Jun, primary, Gu, Zhengxiang, additional, Jurica, Elizabeth Anne, additional, Wu, Ximao, additional, Haque, Lauren E., additional, Williams, Kristin N., additional, Hernandez, Andres S., additional, Hong, Zhenqiu, additional, Gao, Qi, additional, Dabros, Marta, additional, Davulcu, Akin H., additional, Mathur, Arvind, additional, Rampulla, Richard A., additional, Gupta, Arun Kumar, additional, Jayaram, Ramya, additional, Apedo, Atsu, additional, Moore, Douglas B., additional, Liu, Heng, additional, Kunselman, Lori K., additional, Brady, Edward J., additional, Wilkes, Jason J., additional, Zinker, Bradley A., additional, Cai, Hong, additional, Shu, Yue-Zhong, additional, Sun, Qin, additional, Dierks, Elizabeth A., additional, Foster, Kimberly A., additional, Xu, Carrie, additional, Wang, Tao, additional, Panemangalore, Reshma, additional, Cvijic, Mary Ellen, additional, Xie, Chunshan, additional, Cao, Gary G., additional, Zhou, Min, additional, Krupinski, John, additional, Whaley, Jean M., additional, Robl, Jeffrey A., additional, Ewing, William R., additional, and Ellsworth, Bruce Alan, additional

Published
2018
Full Text
View/download PDF

6. Structural and rate studies of the 1,2-additions of lithium phenylacetylide to lithiated quinazolinones: influence of mixed aggregates on the reaction mechanism

Author

Briggs, Timothy F., Winemiller, Mark D., Collum, David B., Parsons, Rodney L., Jr., Davulcu, Akin H., Harris, Gregory D., Fortunak, Joseph M., and Confalone, Pat N.

Subjects
Chemical inhibitors -- Research, Nuclear magnetic resonance spectroscopy -- Research, Lithium compounds -- Research, Chemistry
Abstract

Using a combination of structural and rate studies, the 1,2-addition of lithium phenylacetylide to quinazolinones was explored. The propinquity of an electrophilic imine moiety and potentially nucleophilic acetylide fragment in mixed dimer 13 is positive.

Published
2004

7. Development of a Concise Multikilogram Synthesis of LPA-1 Antagonist BMS-986020 via a Tandem Borylation–Suzuki Procedure

Author

Smith, Michael J., Lawler, Michael J., Kopp, Nathaniel, Mcleod, Douglas D., Davulcu, Akin H., Lin, Dong, Katipally, Kishta, and Sfouggatakis, Chris

Abstract

The process development for the synthesis of BMS-986020 (1) via a palladium catalyzed tandem borylation/Suzuki reaction is described. Evaluation of conditions culminated in an efficient borylation procedure using tetrahydroxydiboron followed by a tandem Suzuki reaction employing the same commercially available palladium catalyst for both steps. This methodology addressed shortcomings of early synthetic routes and was ultimately used for the multikilogram scale synthesis of the active pharmaceutical ingredient 1. Further evaluation of the borylation reaction showed useful reactivity with a range of substituted aryl bromides and iodides as coupling partners. These findings represent a practical, efficient, mild, and scalable method for borylation.

Published
2024
Full Text
View/download PDF

8. Discovery of Potent and Orally Bioavailable Dihydropyrazole GPR40 Agonists

Author

Shi, Jun, Gu, Zhengxiang, Jurica, Elizabeth Anne, Wu, Ximao, Haque, Lauren E., Williams, Kristin N., Hernandez, Andres S., Hong, Zhenqiu, Gao, Qi, Dabros, Marta, Davulcu, Akin H., Mathur, Arvind, Rampulla, Richard A., Gupta, Arun Kumar, Jayaram, Ramya, Apedo, Atsu, Moore, Douglas B., Liu, Heng, Kunselman, Lori K., Brady, Edward J., Wilkes, Jason J., Zinker, Bradley A., Cai, Hong, Shu, Yue-Zhong, Sun, Qin, Dierks, Elizabeth A., Foster, Kimberly A., Xu, Carrie, Wang, Tao, Panemangalore, Reshma, Cvijic, Mary Ellen, Xie, Chunshan, Cao, Gary G., Zhou, Min, Krupinski, John, Whaley, Jean M., Robl, Jeffrey A., Ewing, William R., and Ellsworth, Bruce Alan

Abstract

G protein-coupled receptor 40 (GPR40) has become an attractive target for the treatment of diabetes since it was shown clinically to promote glucose-stimulated insulin secretion. Herein, we report our efforts to develop highly selective and potent GPR40 agonists with a dual mechanism of action, promoting both glucose-dependent insulin and incretin secretion. Employing strategies to increase polarity and the ratio of sp3/sp2character of the chemotype, we identified BMS-986118 (compound 4), which showed potent and selective GPR40 agonist activity in vitro. In vivo, compound 4demonstrated insulinotropic efficacy and GLP-1 secretory effects resulting in improved glucose control in acute animal models.

Published
2024
Full Text
View/download PDF

9. Discovery of Potent and Orally Bioavailable Dihydropyrazole GPR40 Agonists.

Author

Jun Shi, Zhengxiang Gu, Jurica, Elizabeth Anne, Ximao Wu, Haque, Lauren E., Williams, Kristin N., Hernandez, Andres S., Zhenqiu Hong, Qi Gao, Dabros, Marta, Davulcu, Akin H., Mathur, Arvind, Rampulla, Richard A., Gupta, Arun Kumar, Jayaram, Ramya, Apedo, Atsu, Moore, Douglas B., Heng Liu, Kunselman, Lori K., and Brady, Edward J.

Published
2018
Full Text
View/download PDF

21. Indole Diterpene Synthetic Studies. Total Synthesis of (+)-Nodulisporic Acid F and Construction of the Heptacyclic Cores of (+)-Nodulisporic Acids A and B and (-)-Nodulisporic Acid D.

Author

Smith III, Amos B., Davulcu, Akin H., Young Shin Cho, Ohmoto, Kazuyuki, Kórti, Lászlo, and Ishiyama, Haruaki

Subjects
*ORGANIC acids, *INDOLE, *DITERPENES, *BIOSYNTHESIS, *CYCLIC compounds, *RING formation (Chemistry)
Abstract

A first-generation strategy for construction of (+)-nodulisporic acids A (1) and B (2) is described. The strategy entails union of the eastern and western hemisphere subtargets via the indole synthesis protocol developed in our laboratory. Subsequent elaboration of rings E and F, however, revealed the considerable acid instability of the C(24) hydroxyl, thereby preventing further advancement. Nonetheless, preparation of the heptacyclic core of (+)-nodulisporic acids A and B, the total synthesis of (+)-nodulisporic acid F, the simplest member of the nodulisporic acid family, and elaboration of the heptacyclic core of (-)- nodulisporic acid D were achieved. [ABSTRACT FROM AUTHOR]

Published
2007
Full Text
View/download PDF

22. Indole diterpenoid synthetic studies. Construction of the heptacyclic core of (-)-nodulisporic acid D.

Author

Smith AB 3rd, Davulcu AH, and Kürti L

Subjects
Diterpenes chemistry, Molecular Structure, Stereoisomerism, Diterpenes chemical synthesis, Indoles chemical synthesis, Indoles chemistry
Abstract

[structure: see text] Construction of the heptacyclic core of (-)-nodulisporic acid D, a representative member of a recently discovered class of architecturally complex, ectoparasiticidal indole alkaloids, has been achieved. The modular synthetic strategy comprises an expedient, stereocontrolled synthesis of a tricyclic western hemisphere, in conjunction with union of an eastern hemisphere, exploiting the 2-substituted indole synthetic protocol introduced and developed in our laboratory.

Published
2006
Full Text
View/download PDF

Catalog

Books, media, physical & digital resources
See catalog results