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94497-51-5 | 4-[(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)carbamoyl]benzoic acid
CAS No: 94497-51-5 Catalog No: AG0038IQ MDL No:MFCD00866188
Product Description
Catalog Number:
AG0038IQ
Chemical Name:
4-[(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)carbamoyl]benzoic acid
CAS Number:
94497-51-5
Molecular Formula:
C22H25NO3
Molecular Weight:
351.4388
MDL Number:
MFCD00866188
IUPAC Name:
4-[(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)carbamoyl]benzoic acid
InChI:
InChI=1S/C22H25NO3/c1-21(2)11-12-22(3,4)18-13-16(9-10-17(18)21)23-19(24)14-5-7-15(8-6-14)20(25)26/h5-10,13H,11-12H2,1-4H3,(H,23,24)(H,25,26)
InChI Key:
MUTNCGKQJGXKEM-UHFFFAOYSA-N
SMILES:
O=C(c1ccc(cc1)C(=O)O)Nc1ccc2c(c1)C(C)(C)CCC2(C)C
UNII:
08V52GZ3H9
NSC Number:
608000
Properties
Complexity:
546
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
351.183g/mol
Formal Charge:
0
Heavy Atom Count:
26
Hydrogen Bond Acceptor Count:
3
Hydrogen Bond Donor Count:
2
Isotope Atom Count:
0
Molecular Weight:
351.446g/mol
Monoisotopic Mass:
351.183g/mol
Rotatable Bond Count:
3
Topological Polar Surface Area:
66.4A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
5.4
Literature
| Title | Journal |
|---|---|
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| A112, a tamibarotene dimethylaminoethyl ester, may inhibit human leukemia cell growth more potently than tamibarotene. | Leukemia & lymphoma 20120201 |
| Synthetic retinoid Am80 ameliorates chronic graft-versus-host disease by down-regulating Th1 and Th17. | Blood 20120105 |
| Acitretin, an enhancer of alpha-secretase expression, crosses the blood-brain barrier and is not eliminated by P-glycoprotein. | Neuro-degenerative diseases 20120101 |
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| Oral administration of retinoic acid receptor-alpha/beta-specific ligand Am80 suppresses experimental autoimmune uveoretinitis. | Investigative ophthalmology & visual science 20110301 |
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| Convection-enhanced delivery of a synthetic retinoid Am80, loaded into polymeric micelles, prolongs the survival of rats bearing intracranial glioblastoma xenografts. | The Tohoku journal of experimental medicine 20100801 |
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| Retinoic acid protects human breast cancer cells against etoposide-induced apoptosis by NF-kappaB-dependent but cIAP2-independent mechanisms. | Molecular cancer 20100101 |
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| The ATRA-dependent overexpression of the glutamate transporter EAAC1 requires RARbeta induction. | Biochimica et biophysica acta 20090901 |
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| Retinoic acid receptor stimulation protects midbrain dopaminergic neurons from inflammatory degeneration via BDNF-mediated signaling. | Journal of neurochemistry 20090701 |
| Encapsulation of the synthetic retinoids Am80 and LE540 into polymeric micelles and the retinoids' release control. | Journal of controlled release : official journal of the Controlled Release Society 20090619 |
| Synthetic retinoid AM80 inhibits Th17 cells and ameliorates experimental autoimmune encephalomyelitis. | The American journal of pathology 20090601 |
| Synergistic interactions between the synthetic retinoid tamibarotene and glucocorticoids in human myeloma cells. | Cancer science 20090601 |
| Towards retinoid therapy for Alzheimer's disease. | Current Alzheimer research 20090601 |
| Chemopreventive effect of 4-[3,5-Bis(trimethylsilyl) benzamido] benzoic acid (TAC-101) on MNU-induced colon carcinogenesis in a rat model. | Anticancer research 20090601 |
| Synthetic retinoid Am80 inhibits interaction of KLF5 with RAR alpha through inducing KLF5 dephosphorylation mediated by the PI3K/Akt signaling in vascular smooth muscle cells. | FEBS letters 20090417 |
| The effect of Am-80, a synthetic retinoid, on spinal cord injury-induced motor dysfunction in rats. | Biological & pharmaceutical bulletin 20090201 |
| Oral administration of synthetic retinoid Am80 inhibits the development of type 1 diabetes in non-obese diabetic (NOD) mice. | Biological & pharmaceutical bulletin 20090101 |
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| RARalpha is a regulatory factor for Am-80-induced cell growth inhibition of hematologic malignant cells. | International journal of oncology 20070801 |
| Tamibarotene. | Drugs of today (Barcelona, Spain : 1998) 20070801 |
| All-trans retinoic acid induces in vitro angiogenesis via retinoic acid receptor: possible involvement of paracrine effects of endogenous vascular endothelial growth factor signaling. | Endocrinology 20070301 |
| Induction of class II major histocompatibility complex expression in human multiple myeloma cells by retinoid. | Haematologica 20070101 |
| 4- [3,5-bis(trimethylsilyl)benzamido] benzoic acid (TAC-101) induced fas expression and activated caspase-3 and -8 in a DLD-1 colon cancer cell line. | In vivo (Athens, Greece) 20070101 |
| Epigenetic silencing of occludin promotes tumorigenic and metastatic properties of cancer cells via modulations of unique sets of apoptosis-associated genes. | Cancer research 20060915 |
| [Therapeutic strategies for patients with relapsed acute promyelocytic leukemia]. | [Rinsho ketsueki] The Japanese journal of clinical hematology 20060801 |
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| Synthetic retinoid Am80 reduces scavenger receptor expression and atherosclerosis in mice by inhibiting IL-6. | Arteriosclerosis, thrombosis, and vascular biology 20060501 |
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| Retinoic acid via RARalpha inhibits the expression of 24-hydroxylase in human prostate stromal cells. | Biochemical and biophysical research communications 20051230 |
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| Antimyeloma effects of a novel synthetic retinoid Am80 (Tamibarotene) through inhibition of angiogenesis. | Leukemia 20050601 |
| Expression of the retinoic acid-metabolizing enzyme CYP26A1 limits programmed cell death. | Molecular pharmacology 20050501 |
| 4-[3,5-Bis(trimethylsilyl)benzamido] benzoic acid (TAC-101) induces apoptosis in colon cancer partially through the induction of Fas expression. | In vivo (Athens, Greece) 20050101 |
| Differential modulation of PI3-kinase/Akt pathway during all-trans retinoic acid- and Am80-induced HL-60 cell differentiation revealed by DNA microarray analysis. | Biochemical pharmacology 20041201 |
| A synthetic retinoid Am80 (tamibarotene) rescues the memory deficit caused by scopolamine in a passive avoidance paradigm. | Biological & pharmaceutical bulletin 20041101 |
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| Design and synthesis of cyclic urea compounds: a pharmacological study for retinoidal activity. | Bioorganic & medicinal chemistry letters 20040816 |
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| Re-induction of complete remission with a new synthetic retinoid, Am-80, for relapse of acute promyelocytic leukaemia previously treated with all-trans retinoic acid. | British journal of haematology 19970401 |
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