51359-79-6Relevant academic research and scientific papers
Synthesis and Properties of New Cationic-Periphery Porphyrins, Tetrakis(p-(aminomethyl)phenyl)porphyrin and N-Methyltetrakis(p-(aminomethyl)phenyl)porphyrin
Lavallee, David K.,Xu, Zhengjiu,Pina, Richard
, p. 6000 - 6008 (1993)
Two new cationic periphery porphyrins, tetrakis(p-(aminomethyl)phenyl)porphyrin, TAMPP, and N-methyltetrakis(p-(aminomethyl)phenyl)porphyrin, N-MTAMPP, have been synthesized.These porphyrins are protonated in a pH range suitable for studies of binding with nucleic acids.The structure of the N-methylated analogue is significantly different, resulting in a phenomenon that has not been previously reported: the aryl rings at the methine bridge positions of the porphyrin ring undergo restricted rotational motion.The ability of the aryl rings to rotate may be crucial to allow intercalation of cationic periphery porphyrins.The acidity constants and associated pKa's for the porphyrins TAMPP and N-MTAMPP were determined by a combination of spectrophotometric and potentiometric methods.The acid-base properties of these new porphyrins are profoundly altered by N-methylation.The pyrroleninic nitrogen of the free base N-methylated analogue is significantly more basic (at an ionic strength of 0.12 M, the apparent pKa's for deprotonation of TAMPP with all four central nitrogen atoms protonated and the form with three protonated are the same, 8.8, while for N-MTAMPP, these pKa's are 2.4 and 8.1, respectively).As a result, the N-methylated species bears an additional positive charge in the neutral pH region where binding studies with nucleic acids are normally carried out.The peripheral amino groups of the N-methylated porphyrin are more basic as well, by 1.5 pH units at an ionic stength of 0.12 M.
CHEMOKINE CXCR4 RECEPTOR MODULATORS AND USES RELATED THERETO
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, (2018/09/19)
The disclosure relates to chemokine CXCR4 receptor modulators and uses related thereto. The receptor modulators can be formulated to form pharmaceutical compositions comprising the disclosed compounds or pharmaceutically acceptable salts or prodrugs thereof. The compositions may be used for managing CXCR4 related conditions, typically prevention or treatment of viral infections abnormal cellular proliferation, retinal degeneration, inflammatory diseases, or as an immunostimulant or immunosuppressant or for managing cancer and may be administered with another active ingredient such as an antiviral agent or chemotherapeutic agent.
Discovery of Tetrahydroisoquinoline-Containing CXCR4 Antagonists with Improved in Vitro ADMET Properties
Miller, Eric J.,Jecs, Edgars,Truax, Valarie M.,Katzman, Brooke M.,Tahirovic, Yesim A.,Wilson, Robert J.,Kuo, Katie M.,Kim, Michelle B.,Nguyen, Huy H.,Saindane, Manohar T.,Zhao, Huanyu,Wang, Tao,Sum, Chi S.,Cvijic, Mary E.,Schroeder, Gretchen M.,Wilson, Lawrence J.,Liotta, Dennis C.
, p. 946 - 979 (2018/02/17)
CXCR4 is a seven-transmembrane receptor expressed by hematopoietic stem cells and progeny, as well as by ≥48 different cancers types. CXCL12, the only chemokine ligand of CXCR4, is secreted within the tumor microenvironment, providing sanctuary for CXCR4+ tumor cells from immune surveillance and chemotherapeutic elimination by (1) stimulating prosurvival signaling and (2) recruiting CXCR4+ immunosuppressive leukocytes. Additionally, distant CXCL12-rich niches attract and support CXCR4+ metastatic growths. Accordingly, CXCR4 antagonists can potentially obstruct CXCR4-mediated prosurvival signaling, recondition the CXCR4+ leukocyte infiltrate from immunosuppressive to immunoreactive, and inhibit CXCR4+ cancer cell metastasis. Current small molecule CXCR4 antagonists suffer from poor oral bioavailability and off-target liabilities. Herein, we report a series of novel tetrahydroisoquinoline-containing CXCR4 antagonists designed to improve intestinal absorption and off-target profiles. Structure-activity relationships regarding CXCR4 potency, intestinal permeability, metabolic stability, and cytochrome P450 inhibition are presented.
BASIC AMINE COMPOUND AND USE THEREOF
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Page/Page column 16, (2010/11/24)
Novel amine compounds which are represented by the following formula (1) and efficacious against diseases such as a viral infectious disease with HIV, rheumatism, and cancer metastasis; typically, A 1 and A 2 represent a hydrogen atom or a substitutable monocyclic or polycyclic heteroaromatic ring and W represents a substitutable benzene ring or any group represented by the following formula (10) or (11): where X represents O, CH 2 , C(=O), NR 11 , or CHR 35 and D represents a group represented by the following formula (6): where Q represents a single bond, NR 12 , or a group represented by the formula (13): and Y represents a group represented by the following formula (7) : where z represents a substitutable monocyclic or polycyclic aromatic ring; and B represents -NR 25 R 26 ; and R 1 to R 26 in the above formulae represent a hydrogen atom, an alkyl group, an alkenyl group, or an alkynyl group.
AMINE COMPOUNDS AND USE THEREOF
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Page/Page column 48, (2010/02/12)
It is intended to provide novel amine compounds which are efficacious against diseases such as infection with HIV virus, rheumatism and cancer metastasis. Namely, amine compounds represented by the following general formula (1):In a typical case, A1 and A2 represent each an optionally substituted monocyclic or polycyclic aromatic heterocycle; W represents cyclic C3-10 alkylene, an optionally substituted monocyclic or polycyclic aromatic heterocycle, a monocyclic or polycyclic aromatic ring or a partly saturated polycyclic aromatic ring; X represents O, CH2, C(=O) or NR11; and D is a group represented by the following general formula (4) or (6).-Q-Y-BIn the formula (6), Q represents a single bond, S, O or NR12; and Y is a group represented by the following general formula (7). z represents an optionally substituted monocyclic or polycyclic aromatic ring. In the formula (6), B represents NR25R26. In the above formulae, R1 to R26 each represents hydrogen, alkyl, alkenyl or alkynyl.
