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| | 4-[(5,6,7,8-TETRAHYDRO-5,5,8,8-TETRAMETHYL-2-NAPHTHALENYL)CARBOXAMIDO]BENZOIC ACID Basic information |
| Product Name: | 4-[(5,6,7,8-TETRAHYDRO-5,5,8,8-TETRAMETHYL-2-NAPHTHALENYL)CARBOXAMIDO]BENZOIC ACID | | Synonyms: | 4-[[(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)carbonyl]amino]benzoic acid;NSC 608001;4-{[(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)carbonyl]amino}benzoic acid;benzoicacid,4-((5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)carbony;l)amino-;ro40-6055;AM 580;4-[(5,6,7,8-TETRAHYDRO-5,5,8,8-TETRAMETHYL-2-NAPHTHALENYL)CARBOXAMIDO]BENZOIC ACID | | CAS: | 102121-60-8 | | MF: | C22H25NO3 | | MW: | 351.44 | | EINECS: | | | Product Categories: | Intracellular receptor | | Mol File: | 102121-60-8.mol | ![4-[(5,6,7,8-TETRAHYDRO-5,5,8,8-TETRAMETHYL-2-NAPHTHALENYL)CARBOXAMIDO]BENZOIC ACID Structure](CAS/GIF/102121-60-8.gif) |
| | 4-[(5,6,7,8-TETRAHYDRO-5,5,8,8-TETRAMETHYL-2-NAPHTHALENYL)CARBOXAMIDO]BENZOIC ACID Chemical Properties |
| Melting point | 265-267℃ | | Boiling point | 485.24°C (rough estimate) | | density | 1.154 | | refractive index | 1.5614 (estimate) | | storage temp. | -20°C | | solubility | Soluble in DMSO (20mg/ml) or ethanol (10mg/ml). | | form | White to off-white solid. | | pka | 4.28±0.10(Predicted) | | color | Off-white | | Stability: | Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months. |
| WGK Germany | 3 | | RTECS | DH6834890 | | HS Code | 2924.29.7790 |
| | 4-[(5,6,7,8-TETRAHYDRO-5,5,8,8-TETRAMETHYL-2-NAPHTHALENYL)CARBOXAMIDO]BENZOIC ACID Usage And Synthesis |
| Description | AM-580 (102121-60-8) is a retinoic acid analog acting as a RARα agonist (Kd = 8 nM).1 Induces or blocks differentiation depending on cell type and environment.2,3 In combination with CHIR-99021 it induces differentiation of human induced pluripotent stem cells (iPSCs) into intermediate mesoderm (80% induction rate in 5 days) capable of forming kidney structures.4 AM-580 exhibits anti-angiogenic activity in vivo, and induces differentiation of acute promyelocytic leukemia cells.5,6 | | Uses | Retinoid derivative used for gene expression studies of leukemia-retinoic acid receptor (PHL-RAR) cell line differentiation. AM 580 inhibits tumor proliferation by reducing the level of RARγ and activates RAR β. This receptor increases the expression of disintegrin and metalloprotease. | | Definition | ChEBI: An amidobenzoic acid obtained by formal condensation of the carboxy group of (5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)benzoic acid with the anilino group of 4-aminobenzoic acid. A selective RARalpha agonist. | | General Description | AM580 is a retinobenzoic derivative and a RAR-α (retinoic acid receptor-α) agonist. It stimulates the maturation of granulocytes in NB4 promyelocytic leukemia cell line and APL (acute promyelocytic leukemia) blasts. AM580 suppresses endometrial cancer cell proliferation. | | Biological Activity | An analog of retinoic acid that acts as a selective RAR α agonist (EC 50 values are 0.3, 8.6 and 13 nM for RAR α , RAR β and RAR γ respectively). Significantly induces IL-4, IL-5 and IL-13 and inhibits IL-12 and IFN γ synthesis, and induces cell differentiation with over 7 times the activity of retinoic acid in vitro . | | Synthesis | To a 25 mL round-bottomed flask equipped with a reflux condenser tube was added methyl 4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalene-2-carboxamido)benzoate (0.200 g, 0.547 mmol), methanol (10 mL) and potassium hydroxide (0.122 g, 2.18 mmol). The reaction mixture was stirred under reflux conditions for 16 h and subsequently evaporated to dryness. The residue was partitioned between ethyl acetate and deionized water and adjusted to acidic pH with 6 N hydrochloric acid. the organic layer was separated, washed sequentially with deionized water, saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated by rotary evaporation to afford 4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalene-2-carboxamido)benzoic acid as a white solid (0.151 g, 78% yield ). Molecular weight: 351.43; melting point: 265°C; Rf value: 0.3 (ethyl acetate:cyclohexane=50:50).1H NMR (CDCl3, δ): 1.32 (s, 6H, 2×CH3), 1.34 (s, 6H, 2×CH3), 1.73 (s, 4H, 2×CH2), 7.43 (d, 1H, J=8.53 Hz. ArH), 7.57 (d, 1H, J=8.25 Hz, J=1.98 Hz, ArH), 7.78 (d, 2H, J=8.74 Hz, ArH), 7.88 (d, 1H, J=8.74 Hz, ArH), 7.92 (s, 1H, NH), 8.13 (d, 2H, J=8.70 Hz, ArH), and no observed carboxylic acid proton signal.MS-ESI: m/z (relative intensity) 352.1 ([M+H]+, 100).HPLC analysis (Method A, detection wavelength 254 nm): retention time = 6.66 min, peak area = 96.3%. | | storage | Store at RT | | References | [1] BRUNO A. BERNARD . Identification of synthetic retinoids with selectivity for human nuclear retinoic acid receptor γ[J]. Biochemical and biophysical research communications, 1992, 186 2: Pages 977-983. DOI:10.1016/0006-291x(92)90842-9
[2] SAFONOVA I. Fatty Acids and Retinoids Act Synergistically on Adipose Cell Differentiation[J]. Biochemical and biophysical research communications, 1994, 204 2: Pages 498-504. DOI:10.1006/bbrc.1994.2487
[3] NATSUKO SHIBUYA. Retinoic acid is a potential negative regulator for differentiation of human periodontal ligament cells[J]. Journal of periodontal research, 2005, 40 6: 432-440. DOI:10.1111/j.1600-0765.2005.00811.x
[4] TOSHIKAZU ARAOKA. Efficient and rapid induction of human iPSCs/ESCs into nephrogenic intermediate mesoderm using small molecule-based differentiation methods.[J]. ACS Applied Bio Materials, 2014: e84881. DOI:10.1371/journal.pone.0084881
[5] TSUTOMU OIKAWA . Three novel synthetic retinoids, Re 80, Am 580 and Am 80, all exhibit anti-angiogenic activity in vivo[J]. European journal of pharmacology, 1993, 249 1: Pages 113-116. DOI:10.1016/0014-2999(93)90669-9
[6] M GIANNÍ. AM580, a stable benzoic derivative of retinoic acid, has powerful and selective cyto-differentiating effects on acute promyelocytic leukemia cells.[J]. Blood, 1996, 87 4: 1520-1531. |
| | 4-[(5,6,7,8-TETRAHYDRO-5,5,8,8-TETRAMETHYL-2-NAPHTHALENYL)CARBOXAMIDO]BENZOIC ACID Preparation Products And Raw materials |
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