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Article: 4-Bromo-2H-1,3-oxazine-2,6(3H)-dione.

Parrish, Damon / Tivitmahaisoon, Parcharee / Rehberg, Gretchen M / Kastner, Margaret E

Acta crystallographica. Section E, Structure reports online

2009 Volume 65, Issue Pt 10, Page(s) o2355

Abstract: The title compound, C(4)H(2)BrNO(3), is one of a series of three substituted oxauracils prepared as precursors in the preparation of 1-aza-1,3-butadienes. Although each structure has identical potential for N-H⋯O inter-molecular hydrogen bonds, each ... ...

Abstract	The title compound, C(4)H(2)BrNO(3), is one of a series of three substituted oxauracils prepared as precursors in the preparation of 1-aza-1,3-butadienes. Although each structure has identical potential for N-H⋯O inter-molecular hydrogen bonds, each forms a distinctive inter-molecular network. In the title compound, there are two independent mol-ecules in the asymmetric unit, with a non-crystallographic twofold screw-like relationship between them. The two indpendent mol-ecules are linked by an inter-molecular N-H⋯O hydrogen bond. In the crystal structure, this hydrogen-bonded pair is linked to translationally related mol-ecules through further inter-molecular N-H⋯O hydrogen bonds, forming one-dimensional chains along [100]. The crystal structure also has short Br⋯O=C inter-molecular contacts with distances of 2.843 (4) and 2.852 (4) Å.
Language	English
Publishing date	2009-09-05
Publishing country	United States
Document type	Journal Article
ZDB-ID	2041947-8
ISSN	1600-5368
ISSN	1600-5368
DOI	10.1107/S1600536809034631
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Article ; Online: Potent GCN2 Inhibitor Capable of Reversing MDSC-Driven T Cell Suppression Demonstrates In Vivo Efficacy as a Single Agent and in Combination with Anti-Angiogenesis Therapy.

Jackson, Jeffrey J / Shibuya, Grant M / Ravishankar, Buvana / Adusumilli, Lavanya / Bradford, Delia / Brockstedt, Dirk G / Bucher, Cyril / Bui, Minna / Cho, Cynthia / Colas, Christoph / Cutler, Gene / Dukes, Adrian / Han, Xinping / Hu, Dennis X / Jacobson, Scott / Kassner, Paul D / Katibah, George E / Ko, Michelle Yoo Min / Kolhatkar, Urvi /

Journal of medicinal chemistry

2022 Volume 65, Issue 19, Page(s) 12895–12924

Abstract: General control nonderepressible 2 (GCN2) protein kinase is a cellular stress sensor within the tumor microenvironment (TME), whose signaling cascade has been proposed to contribute to immune escape in tumors. Herein, we report the discovery of cell- ... ...

Abstract	General control nonderepressible 2 (GCN2) protein kinase is a cellular stress sensor within the tumor microenvironment (TME), whose signaling cascade has been proposed to contribute to immune escape in tumors. Herein, we report the discovery of cell-potent GCN2 inhibitors with excellent selectivity against its closely related Integrated Stress Response (ISR) family members heme-regulated inhibitor kinase (HRI), protein kinase R (PKR), and (PKR)-like endoplasmic reticulum kinase (PERK), as well as good kinome-wide selectivity and favorable PK. In mice, compound
MeSH term(s)	Animals ; Heme ; Mice ; Mice, Knockout ; Myeloid-Derived Suppressor Cells ; Protein Serine-Threonine Kinases ; T-Lymphocytes/metabolism ; eIF-2 Kinase/metabolism
Chemical Substances	Heme (42VZT0U6YR) ; Protein Serine-Threonine Kinases (EC 2.7.11.1) ; eIF-2 Kinase (EC 2.7.11.1)
Language	English
Publishing date	2022-09-20
Publishing country	United States
Document type	Journal Article
ZDB-ID	218133-2
ISSN	1520-4804 ; 0022-2623
ISSN (online)	1520-4804
ISSN	0022-2623
DOI	10.1021/acs.jmedchem.2c00736
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Article: Fragment-Based Drug Design of Novel Pyranopyridones as Cell Active and Orally Bioavailable Tankyrase Inhibitors.

de Vicente, Javier / Tivitmahaisoon, Parcharee / Berry, Pamela / Bolin, David R / Carvajal, Daisy / He, Wei / Huang, Kuo-Sen / Janson, Cheryl / Liang, Lena / Lukacs, Christine / Petersen, Ann / Qian, Hong / Yi, Lin / Zhuang, Yong / Hermann, Johannes C

ACS medicinal chemistry letters

2015 Volume 6, Issue 9, Page(s) 1019–1024

Abstract: Tankyrase activity has been linked to the regulation of intracellular axin levels, which have been shown to be crucial for the Wnt pathway. Deregulated Wnt signaling is important for the genesis of many diseases including cancer. We describe herein the ... ...

Abstract	Tankyrase activity has been linked to the regulation of intracellular axin levels, which have been shown to be crucial for the Wnt pathway. Deregulated Wnt signaling is important for the genesis of many diseases including cancer. We describe herein the discovery and development of a new series of tankyrase inhibitors. These pyranopyridones are highly active in various cell-based assays. A fragment/structure based optimization strategy led to a compound with good pharmacokinetic properties that is suitable for in vivo studies and further development.
Language	English
Publishing date	2015-08-04
Publishing country	United States
Document type	Journal Article
ISSN	1948-5875
ISSN	1948-5875
DOI	10.1021/acsmedchemlett.5b00251
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Article: Fluorogenic peptide sequences--transformation of short peptides into fluorophores under ambient photooxidative conditions.

Juskowiak, Gary L / Stachel, Shawn J / Tivitmahaisoon, Parcharee / Van Vranken, David L

Journal of the American Chemical Society

2004 Volume 126, Issue 2, Page(s) 550–556

Abstract: Long-lived proteins are susceptible to nonenzymatic chemical reactions and the evolution of fluorescence; however, little is known about the sequence-dependence of fluorogenesis. We synthesized a library of over half a million octapeptides and exposed it ...

Abstract	Long-lived proteins are susceptible to nonenzymatic chemical reactions and the evolution of fluorescence; however, little is known about the sequence-dependence of fluorogenesis. We synthesized a library of over half a million octapeptides and exposed it to light and air in pH 7.4 buffer to identify fluorogenic peptides that evolve under mild oxidative conditions. The bead-based peptide library was composed of the general sequence H(2)N-Ala-(Xxx)(6)-Ala-resin, where Xxx was one of nine representative amino acids: Asp, Gly, His, Leu, Lys, Pro, Ser, Trp, and Tyr. Next, we selected five highly fluorescent beads from the library and subjected them to microsequencing, revealing the sequence of the unreacted peptide. All five of the fluorogenic sequences were ionic; lacked Tyr, His, and Leu; and most of the sequences contained only one Trp. We then synthesized the five soluble peptides corresponding to the fluorogenic peptide sequences and exposed them to photooxidative conditions. In general, the soluble peptides reacted slowly, generating nonfluorescent monooxygenated and dioxygenated products. However, one peptide (H(2)N-AlaLysProTrpGlyGlyAspAla-CONH(2)) evolved into a highly fluorescent photoproduct as well as a nonfluorescent monooxygenated photoproduct. The fluorescent photoproduct consisted of a 2-carboxy-quinolin-4-yl moiety fused to the N-terminus of GlyGlyAspAla. The formation of this photoproduct requires cleavage of the peptide backbone and a dramatic reorganization of tryptophan. This work demonstrates that sequencing unreacted peptide on beads can reveal sequences with unique nonenzymatic reactivity. The study also confirms that peptide fluorogenesis is dependent on sequence and not merely on the presence of tryptophan. The potential importance of fluorogenic peptide sequences is two-fold. First, fluorogenic sequences that arise through mutation could prove to be hot spots for human aging. Second, fluorogenic sequences, particularly those compatible with intracellular conditions, may serve as fluorescent tags for proteins or as fluorescent biomaterials.
MeSH term(s)	Amino Acid Sequence ; Fluorescence ; Fluorescent Dyes/chemistry ; Oligopeptides/chemistry ; Oligopeptides/radiation effects ; Oxidation-Reduction ; Peptide Library ; Photochemistry
Chemical Substances	Fluorescent Dyes ; Oligopeptides ; Peptide Library
Language	English
Publishing date	2004-01-02
Publishing country	United States
Document type	Journal Article ; Research Support, Non-U.S. Gov't ; Research Support, U.S. Gov't, P.H.S.
ZDB-ID	3155-0
ISSN	1520-5126 ; 0002-7863
ISSN (online)	1520-5126
ISSN	0002-7863
DOI	10.1021/ja0379971
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Article ; Online: Scaffold hopping towards potent and selective JAK3 inhibitors: discovery of novel C-5 substituted pyrrolopyrazines.

de Vicente, Javier / Lemoine, Remy / Bartlett, Mark / Hermann, Johannes C / Hekmat-Nejad, Mohammad / Henningsen, Robert / Jin, Sue / Kuglstatter, Andreas / Li, Hongju / Lovey, Allen J / Menke, John / Niu, Linghao / Patel, Vaishali / Petersen, Ann / Setti, Lina / Shao, Ada / Tivitmahaisoon, Parcharee / Vu, Minh Diem / Soth, Michael

Bioorganic & medicinal chemistry letters

2014 Volume 24, Issue 21, Page(s) 4969–4975

Abstract: The discovery of a novel series of pyrrolopyrazines as JAK inhibitors with comparable enzyme and cellular activity to tofacitinib is described. The series was identified using a scaffold hopping approach aided by structure based drug design using ... ...

Abstract	The discovery of a novel series of pyrrolopyrazines as JAK inhibitors with comparable enzyme and cellular activity to tofacitinib is described. The series was identified using a scaffold hopping approach aided by structure based drug design using principles of intramolecular hydrogen bonding for conformational restriction and targeting specific pockets for modulating kinase activity.
MeSH term(s)	Drug Design ; Humans ; Janus Kinase 3/antagonists & inhibitors ; Janus Kinase 3/metabolism ; Models, Molecular ; Molecular Conformation ; Molecular Structure ; Phosphorylation ; Piperidines/pharmacology ; Protein Kinase Inhibitors/chemistry ; Protein Kinase Inhibitors/pharmacology ; Pyrazines/chemistry ; Pyrimidines/pharmacology ; Pyrroles/chemistry ; Pyrroles/pharmacology ; Structure-Activity Relationship
Chemical Substances	Piperidines ; Protein Kinase Inhibitors ; Pyrazines ; Pyrimidines ; Pyrroles ; tofacitinib (87LA6FU830) ; Janus Kinase 3 (EC 2.7.10.2)
Language	English
Publishing date	2014-11-01
Publishing country	England
Document type	Comparative Study ; Journal Article
ZDB-ID	1063195-1
ISSN	1464-3405 ; 0960-894X
ISSN (online)	1464-3405
ISSN	0960-894X
DOI	10.1016/j.bmcl.2014.09.031
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Article ; Online: Strategic use of conformational bias and structure based design to identify potent JAK3 inhibitors with improved selectivity against the JAK family and the kinome.

Lynch, Stephen M / DeVicente, Javier / Hermann, Johannes C / Jaime-Figueroa, Saul / Jin, Sue / Kuglstatter, Andreas / Li, Hongju / Lovey, Allen / Menke, John / Niu, Linghao / Patel, Vaishali / Roy, Douglas / Soth, Michael / Steiner, Sandra / Tivitmahaisoon, Parcharee / Vu, Minh Diem / Yee, Calvin

Bioorganic & medicinal chemistry letters

2013 Volume 23, Issue 9, Page(s) 2793–2800

Abstract: Using a structure based design approach we have identified a series of indazole substituted pyrrolopyrazines, which are potent inhibitors of JAK3. Intramolecular electronic repulsion was used as a strategy to induce a strong conformational bias within ... ...

Abstract	Using a structure based design approach we have identified a series of indazole substituted pyrrolopyrazines, which are potent inhibitors of JAK3. Intramolecular electronic repulsion was used as a strategy to induce a strong conformational bias within the ligand. Compounds bearing this conformation participated in a favorable hydrophobic interaction with a cysteine residue in the JAK3 binding pocket, which imparted high selectivity versus the kinome and improved selectivity within the JAK family.
MeSH term(s)	Binding Sites ; Crystallography, X-Ray ; Drug Design ; Hydrophobic and Hydrophilic Interactions ; Indazoles/chemistry ; Janus Kinase 1/antagonists & inhibitors ; Janus Kinase 1/metabolism ; Janus Kinase 2/antagonists & inhibitors ; Janus Kinase 2/metabolism ; Janus Kinase 3/antagonists & inhibitors ; Janus Kinase 3/metabolism ; Molecular Docking Simulation ; Protein Binding ; Protein Kinase Inhibitors/chemical synthesis ; Protein Kinase Inhibitors/chemistry ; Protein Kinase Inhibitors/metabolism ; Protein Structure, Tertiary ; Pyrazines/chemical synthesis ; Pyrazines/chemistry ; Pyrazines/metabolism ; Structure-Activity Relationship
Chemical Substances	Indazoles ; Protein Kinase Inhibitors ; Pyrazines ; Janus Kinase 1 (EC 2.7.10.2) ; Janus Kinase 2 (EC 2.7.10.2) ; Janus Kinase 3 (EC 2.7.10.2)
Language	English
Publishing date	2013-05-01
Publishing country	England
Document type	Journal Article
ZDB-ID	1063195-1
ISSN	1464-3405 ; 0960-894X
ISSN (online)	1464-3405
ISSN	0960-894X
DOI	10.1016/j.bmcl.2013.02.012
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Article: Strategic use of conformational bias and structure based design to identify potent JAK3 inhibitors with improved selectivity against the JAK family and the kinome

Bioorganic & medicinal chemistry letters. 2013 May 1, v. 23, no. 9

2013

Abstract	Using a structure based design approach we have identified a series of indazole substituted pyrrolopyrazines, which are potent inhibitors of JAK3. Intramolecular electronic repulsion was used as a strategy to induce a strong conformational bias within the ligand. Compounds bearing this conformation participated in a favorable hydrophobic interaction with a cysteine residue in the JAK3 binding pocket, which imparted high selectivity versus the kinome and improved selectivity within the JAK family.
Keywords	bias ; cysteine ; enzyme inhibitors ; genome ; hydrophobic bonding ; molecular conformation ; non-specific protein-tyrosine kinase ; structure-activity relationships
Language	English
Dates of publication	2013-0501
Size	p. 2793-2800.
Publishing place	Elsevier Ltd
Document type	Article
ZDB-ID	1063195-1
ISSN	1464-3405 ; 0960-894X
ISSN (online)	1464-3405
ISSN	0960-894X
DOI	10.1016/j.bmcl.2013.02.012
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Article: Total Synthesis of 6-Deoxypladienolide D and Assessment of Splicing Inhibitory Activity in a Mutant SF3B1 Cancer Cell Line

Arai, Kenzo / Buonamici Silvia / Chan Betty / Corson Laura / Endo Atsushi / Gerard Baudouin / Hao Ming-Hong / Karr Craig / Kira Kazunobu / Lee Linda / Liu Xiang / Lowe Jason T / Luo Tuoping / Marcaurelle Lisa A / Mizui Yoshiharu / Nevalainen Marta / OâShea Morgan Welzel / Park Eun Sun / Perino Samantha A /

Prajapati Sudeep / Shan Mingde / Smith Peter G / Tivitmahaisoon Parcharee / Wang John Yuan / Warmuth Markus / Wu Kuo-Ming / Yu Lihua / Zhang Huiming / Zheng Guo-Zhu / Keaney Gregg F

Organic letters. 2014 Nov. 07, v. 16, no. 21

2014

Abstract: A total synthesis of the natural product 6-deoxypladienolide D (1) has been achieved. Two noteworthy attributes of the synthesis are (1) a late-stage allylic oxidation which proceeds with full chemo-, regio-, and diastereoselectivity and (2) the ... ...

Abstract	A total synthesis of the natural product 6-deoxypladienolide D (1) has been achieved. Two noteworthy attributes of the synthesis are (1) a late-stage allylic oxidation which proceeds with full chemo-, regio-, and diastereoselectivity and (2) the development of a scalable and cost-effective synthetic route to support drug discovery efforts. 6-Deoxypladienolide D (1) demonstrates potent growth inhibition in a mutant SF3B1 cancer cell line, high binding affinity to the SF3b complex, and inhibition of pre-mRNA splicing.
Keywords	binding capacity ; chemical structure ; cost effectiveness ; diastereoselectivity ; drugs ; growth retardation ; mutants ; neoplasms ; organic compounds ; oxidation
Language	English
Dates of publication	2014-1107
Size	p. 5560-5563.
Publishing place	American Chemical Society
Document type	Article
ISSN	1523-7052
DOI	10.1021%2Fol502556c
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Article: Development of amino-pyrimidine inhibitors of c-Jun N-terminal kinase (JNK): Kinase profiling guided optimization of a 1,2,3-benzotriazole lead

Palmer, Wylie S / Alam, Muzaffar / Arzeno, Humberto B / Chang, Kung-Ching / Dunn, James P / Goldstein, David M / Gong, Leyi / Goyal, Bindu / Hermann, Johannes C / Hogg, J. Heather / Hsieh, Gary / Jahangir, Alam / Janson, Cheryl / Jin, Sue / Ursula Kammlott, R / Kuglstatter, Andreas / Lukacs, Christine / Michoud, Christophe / Niu, Linghao /

Reuter, Deborah C / Shao, Ada / Silva, Tania / Trejo-Martin, Teresa A / Stein, Karin / Tan, Yun-Chou / Tivitmahaisoon, Parcharee / Tran, Patricia / Wagner, Paul / Weller, Paul / Wu, Shao-Yong

Bioorganic & medicinal chemistry letters. 2013 Mar. 1, v. 23, no. 5

2013

Abstract: A series of amino-pyrimidines was developed based upon an initial kinase cross-screening hit from a CDK2 program. Kinase profiling and structure-based drug design guided the optimization from the initial 1,2,3-benzotriazole hit to a potent and selective ... ...

Abstract	A series of amino-pyrimidines was developed based upon an initial kinase cross-screening hit from a CDK2 program. Kinase profiling and structure-based drug design guided the optimization from the initial 1,2,3-benzotriazole hit to a potent and selective JNK inhibitor, compound 24f (JNK1 and 2 IC₅₀=16 and 66nM, respectively), with bioavailability in rats and suitable for further in vivo pharmacological evaluation.
Keywords	bioavailability ; chemistry ; cyclin-dependent kinase ; drugs ; mitogen-activated protein kinase ; rats
Language	English
Dates of publication	2013-0301
Size	p. 1486-1492.
Publishing place	Elsevier Ltd
Document type	Article
ZDB-ID	1063195-1
ISSN	1464-3405 ; 0960-894X
ISSN (online)	1464-3405
ISSN	0960-894X
DOI	10.1016/j.bmcl.2012.12.047
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Article ; Online: Total synthesis of 6-deoxypladienolide D and Assessment of Splicing Inhibitory Activity in a Mutant SF3B1 cancer cell line.

Arai, Kenzo / Buonamici, Silvia / Chan, Betty / Corson, Laura / Endo, Atsushi / Gerard, Baudouin / Hao, Ming-Hong / Karr, Craig / Kira, Kazunobu / Lee, Linda / Liu, Xiang / Lowe, Jason T / Luo, Tuoping / Marcaurelle, Lisa A / Mizui, Yoshiharu / Nevalainen, Marta / O'Shea, Morgan Welzel / Park, Eun Sun / Perino, Samantha A /

Prajapati, Sudeep / Shan, Mingde / Smith, Peter G / Tivitmahaisoon, Parcharee / Wang, John Yuan / Warmuth, Markus / Wu, Kuo-Ming / Yu, Lihua / Zhang, Huiming / Zheng, Guo-Zhu / Keaney, Gregg F

Organic letters

2014 Volume 16, Issue 21, Page(s) 5560–5563

Abstract	A total synthesis of the natural product 6-deoxypladienolide D (1) has been achieved. Two noteworthy attributes of the synthesis are (1) a late-stage allylic oxidation which proceeds with full chemo-, regio-, and diastereoselectivity and (2) the development of a scalable and cost-effective synthetic route to support drug discovery efforts. 6-Deoxypladienolide D (1) demonstrates potent growth inhibition in a mutant SF3B1 cancer cell line, high binding affinity to the SF3b complex, and inhibition of pre-mRNA splicing.
MeSH term(s)	Antineoplastic Agents/chemical synthesis ; Antineoplastic Agents/chemistry ; Antineoplastic Agents/pharmacology ; Binding Sites ; Cell Line, Tumor/chemistry ; Cell Line, Tumor/drug effects ; Cell Proliferation/drug effects ; Epoxy Compounds/chemical synthesis ; Epoxy Compounds/chemistry ; Epoxy Compounds/metabolism ; Humans ; Macrolides/chemical synthesis ; Macrolides/chemistry ; Macrolides/metabolism ; Phosphoproteins/antagonists & inhibitors ; Phosphoproteins/chemistry ; RNA Splicing/drug effects ; RNA Splicing Factors ; Ribonucleoprotein, U2 Small Nuclear/antagonists & inhibitors ; Ribonucleoprotein, U2 Small Nuclear/chemistry
Chemical Substances	6-deoxypladienolide D ; Antineoplastic Agents ; Epoxy Compounds ; Macrolides ; Phosphoproteins ; RNA Splicing Factors ; Ribonucleoprotein, U2 Small Nuclear ; SF3B1 protein, human
Language	English
Publishing date	2014-11-07
Publishing country	United States
Document type	Journal Article
ISSN	1523-7052
ISSN (online)	1523-7052
DOI	10.1021/ol502556c
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