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102121-60-8

中文名稱 4-[(5,6,7,8-四氫-5,5,8,8-四甲基-2-萘基)甲酰氨基]苯甲酸
英文名稱 4-[(5,6,7,8-TETRAHYDRO-5,5,8,8-TETRAMETHYL-2-NAPHTHALENYL)CARBOXAMIDO]BENZOIC ACID
CAS 102121-60-8
分子式 C22H25NO3
分子量 351.44
MOL 文件 102121-60-8.mol
更新日期 2025/04/24 17:16:24
102121-60-8 結構式 102121-60-8 結構式

基本信息

中文別名
AM580 AM580
RARΑ激動劑(AM580)
4-(5,5,8,8-四甲基-5,6,7,8-四氫化萘-2-甲酰氨基)苯甲酸
4-[(5,6,7,8-四氫-5,5,8,8-四甲基-2-萘基)甲酰氨基]苯甲酸
英文別名
cd336
AM 580
CS-1051
l)amino-
ro40-6055
NSC 608001
AM580 (CD336)
AM-580
AM 580
CD336
NSC608001
RO 40-6055
4-(1,1,4,4-Tetramethyltetralin-6-ylcarbonylamino)benzoic acid
4-[(5,6,7,8-TETRAHYDRO-5,5,8,8-TETRAMETHYL-2-NAPHTHALENYL)CA...
所屬類別
生物化工:激動劑抑制劑

物理化學性質

熔點265-267℃
沸點485.24°C (rough estimate)
密度1.154
折射率1.5614 (estimate)
儲存條件−20°C
儲存條件-20°C
溶解度溶于DMSO(20mg/ml)或乙醇(10mg/ml)。
酸度系數(pKa)4.28±0.10(Predicted)
形態(tài)白色至類白色固體
顏色米白色
穩(wěn)定性可在-20°C下的DMSO中的溶液儲存長達3個月。
InChI1S/C22H25NO3/c1-21(2)11-12-22(3,4)18-13-15(7-10-17(18)21)19(24)23-16-8-5-14(6-9-16)20(25)26/h5-10,13H,11-12H2,1-4H3,(H,23,24)(H,25,26)
InChIKeySZWKGOZKRMMLAJ-UHFFFAOYSA-N
SMILESCC1(C)CCC(C)(C)c2cc(ccc12)C(=O)Nc3ccc(cc3)C(O)=O

制備方法

方法1
Benzoic acid, 4-[[(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)carbonyl]amino]-, methyl ester

102121-59-5

4-[(5,6,7,8-四氫-5,5,8,8-四甲基-2-萘基)甲酰氨基]苯甲酸

102121-60-8

向裝有回流冷凝管的25 mL圓底燒瓶中加入4-(5,6,7,8-四氫-5,5,8,8-四甲基萘-2-甲酰胺基)苯甲酸甲酯(0.200 g,0.547 mmol)、甲醇(10 mL)和氫氧化鉀(0.122 g,2.18 mmol)。將反應混合物在回流條件下攪拌16小時,隨后蒸發(fā)至干。將殘余物在乙酸乙酯和去離子水之間分配,用6N鹽酸調節(jié)至酸性pH。分離有機層,依次用去離子水、飽和食鹽水洗滌,無水硫酸鈉干燥,過濾后旋轉蒸發(fā)濃縮,得到4-(5,6,7,8-四氫-5,5,8,8-四甲基萘-2-甲酰胺基)苯甲酸,為白色固體(0.151 g,收率78%)。分子量:351.43;熔點:265°C;Rf值:0.3(乙酸乙酯:環(huán)己烷=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),未觀察到羧酸質子信號。MS-ESI:m/z(相對強度)352.1([M+H]+,100)。HPLC分析(方法A,檢測波長254 nm):保留時間=6.66分鐘,峰面積=96.3%。

參考文獻:

[1] Patent: EP1541549, 2005, A1. Location in patent: Page/Page column 13-14; 37

[2] Journal of Medicinal Chemistry, 1988, vol. 31, # 11, p. 2182 - 2192

[3] Chemical and Pharmaceutical Bulletin, 1986, vol. 34, # 5, p. 2275 - 2278

安全數據

WGK Germany3
WGK Germany3
RTECS號DH6834890
海關編碼2924.29.7790
存儲類別11 - Combustible Solids
4-[(5,6,7,8-四氫-5,5,8,8-四甲基-2-萘基)甲酰氨基]苯甲酸價格(試劑級)
報價日期產品編號產品名稱CAS號包裝價格
2026/06/06A3082AM580
AM580
102121-60-85mg120元
2026/06/06A3082AM580
AM580
102121-60-8100mg1350元
2026/06/05HY-10475R4-[(5,6,7,8-四氫-5,5,8,8-四甲基-2-萘基)甲酰氨基]苯甲酸
AM580 (Standard)
102121-60-85 mg1680元

常見問題列表

生物活性
AM580是視黃酸核受體(RAR)激動劑,對RARα, RARβ和RARγ的Kd值分別為8 nM, 131 nM 和450 nM。
體外研究

In the presence of G-CSF, AM580 (at 10 -8 M) produces a remarkable induction in LAP mRNA of NB4 cells. At a concentration of 10 -5 M, AM580 and ATRA, in combination with G-CSF, induce almost the same level of LAP transcript. AM580 (at 10 -8 M) leads to an approximately sixfold increase in the steady-state levels of the transcript coding for the G-CSF receptor in NB4 cells. AM580 (50 nM) increases caspase-3 expression in all of the colonies, and in 30% of the colonies induce acinar-like cavitation. Knockdown of RARγ1 in primary Myc cells using shRARγ1 followed by Am580 treatment results in an even higher level of CRBP1 expression, showing that in these cells RARγ has a repressive effect on the RARα target gene CRBP1 . Am580 (200 nM) enhances the anti-proliferative effect exhibited by RARγ knockdown in the MCF-10A and MCF-7 cell lines but not in the MDA-MB-231 cells.

體內研究

Am580 (0.3 mg/kg/day) treatment has a more profound effect on tumor-free survival of MMTV-wnt1 mice, the effect being noticeable even in early appearing tumors, and no overt toxicity is found in liver, lungs, kidney, and spleen. Am580 treatment reduces substantially and equally the level of hyperplasia in both transgenic glands. Treatment of MMTV-Myc mice with the RARα-selective agonist Am580 leads to significant inhibition of mammary tumor growth, lung metastasis and extends tumor latency in 63% of mice.

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