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塞曲司特

塞曲司特用途

Seratrodast(AA 2414)是血栓素A2受体(TP)拮抗剂。

塞曲司特名称

[ CAS 号 ]:
112665-43-7

[ 中文名 ]:
塞曲司特

[ 英文名 ]:
Seratrodast

[中文别名 ]:

西拉达司

[英文别名 ]:

Bronica
MFCD00875701

塞曲司特生物活性

[ 描述 ]:

Seratrodast(AA 2414)是血栓素A2受体(TP)拮抗剂。

[ 相关类别 ]:

信号通路 >> G 蛋白偶联受体/G 蛋白 >> 前列腺素受体

研究领域 >> 炎症/免疫

[参考文献]

[1]. Ashida, Y., et al., A novel anti-asthmatic quinone derivative, AA-2414 with a potent antagonistic activity against a variety of spasmogenic prostanoids. Prostaglandins, 1989. 38(1): p. 91-112.

[2]. Walsh, S.W., Y. Wang, and A. Killian, AA-2414, an antioxidant and thromboxane receptor blocker, completely inhibits peroxide-induced vasoconstriction in the human placenta. J Pharmacol Exp Ther, 1999. 290(1): p. 220-6.

[相关活性小分子]

塞曲司特物理化学性质

[ 密度 ]:
1.1±0.1 g/cm3

[ 沸点 ]:
522.3±49.0 °C at 760 mmHg

[ 熔点 ]:
118-120°C

[ 分子式 ]:
C₂₂H₂₆O₄

[ 分子量 ]:
354.439

[ 闪点 ]:
283.8±26.3 °C

[ 精确质量 ]:
354.183105

[ PSA ]:
71.44000

[ LogP ]:
5.25

[ 外观性状 ]:
淡橙色固体

[ 蒸汽压 ]:
0.0±1.4 mmHg at 25°C

[ 折射率 ]:
1.555

[ 储存条件 ]:
Store at +4°C

塞曲司特MSDS

塞曲司特毒性和生态

CHEMICAL IDENTIFICATION

RTECS NUMBER :: DA1600050

CHEMICAL NAME :: Bezeneheptanoic acid, beta-(2,4,5-trimethyl-3,6-dioxo-1,4-cyclohexadien-1-y l)-, (+-)-

CAS REGISTRY NUMBER :: 112665-43-7

LAST UPDATED :: 199703

DATA ITEMS CITED :: 9

MOLECULAR FORMULA :: C22-H26-O4

MOLECULAR WEIGHT :: 354.48

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 3750 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 26,953,1995

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1350 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 26,953,1995

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >5 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 26,953,1995

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1520 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 26,953,1995

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1100 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 26,953,1995

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >5 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 26,953,1995 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 3600 mg/kg

SEX/DURATION :: female 6-17 day(s) after conception

TOXIC EFFECTS :: Reproductive - Maternal Effects - other effects Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Effects on Embryo or Fetus - fetal death

REFERENCE :: YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 23,2939,1995

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 3600 mg/kg

SEX/DURATION :: female 6-17 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - musculoskeletal system Reproductive - Specific Developmental Abnormalities - cardiovascular (circulatory) system Reproductive - Effects on Newborn - behavioral

REFERENCE :: YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 23,2939,1995

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 900 mg/kg

SEX/DURATION :: female 9-11 day(s) after conception

TOXIC EFFECTS :: Reproductive - Maternal Effects - other effects

REFERENCE :: YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 23,2939,1995

塞曲司特安全信息

[ 符号 ]:

GHS08

[ 信号词 ]:
Warning

[ 危害声明 ]:
H361d

[ 警示性声明 ]:
P201-P308 + P313

[ 危害码 (欧洲) ]:
Xi

[ 风险声明 (欧洲) ]:
R36/37/38:Irritating to eyes, respiratory system and skin .

[ 安全声明 (欧洲) ]:
S26-S24/25

[ 危险品运输编码 ]:
3336

[ WGK德国 ]:
3

[ RTECS号 ]:
TZ2585500

[ 包装等级 ]:
III

[ 危险类别 ]:
6.1

[ 海关编码 ]:
29309070

塞曲司特合成路线

塞曲司特上下游产品

塞曲司特上游产品

塞曲司特下游产品

塞曲司特制备

2,3,5-三甲基氢醌和7-羟基苯庚酸溶于甲苯,加入D-樟脑-10-磺酸,在70℃下搅拌20h.反应液浓缩后,剩余物用10%三氯化铁水溶液氧化.经处理后,再层析得到产物.

1. 6-氯甲酰基-己酸乙酯的制备

在反应瓶中加入6-(乙氧羰基己酸)120g(0.64mol)(该化合物根据文献[6]合成,bp144~148ºC/666.61Pa)、二氯甲烷200ml,搅拌溶解,于环境温度下往该混合物中加入氯化亚砜92.0ml(1.28mol),混合物升温到50ºC,在此温度下搅拌2h后,减压蒸除溶剂,剩余物减压蒸馏,收集bp90~91ºC/39.9966Pa)馏分,得无色液体129g,收率98%,直接用于下步反应.

2. 7-苯庚酸乙酯-7-酮的制备

在反应瓶中加入苯71ml(0.80mol)和无水三氯化铝53.2(0.20mol),搅拌悬浮,并降温至5ºC,搅拌下滴加6-氯甲酰基-己酸乙酯41.3g(0.2mol),40min滴加完,将混合物升温至90ºC,搅拌反应2h.冷却至室温,反应混合物倾入到碎冰400g/浓盐酸40ml中.搅拌20min后,用乙酸乙酯500ml分3次提取,分出有机层用饱和盐水洗,无水硫酸钠干燥,减压浓缩蒸除溶剂得油状物46.5g.

在反应瓶加入上述油状物46.5g和乙醇200ml,搅拌溶解,往该溶液再加入浓硫酸2ml,将混合物加热至80ºC回流2h.冷却,加入碳酸氢钠水溶液中和,减压浓缩回收乙醇.加入乙酸乙酯400ml提取,分出有机层,饱和盐水,洗涤,干燥,蒸发溶剂后得油状物7-苯庚酸乙酯-7-酮可直接用于下一步反应.

3. 7-羟基-7-苯庚酸乙酯的制备

在反应瓶中加入油状物7-苯庚酸乙酯-7-酮一批量,再加入甲醇300ml,搅拌溶解,冷却至0ºC后,在10min内分批加入NaBH4 4.5g(0.12mol).在其同样的条件下继续搅拌30min.加入丙酮13ml和甲醇,终止反应.减压下浓缩回收甲醇,往剩余物中加入乙酸乙酯400ml和水300ml,分出乙酸乙酯层,盐水洗,干燥,浓缩,得7-羟基-7-苯庚酸乙酯的油状物,可用于下一步反应.

4. 4. 7-羟基-7-苯庚酸的制备

在反应瓶中加入7-羟基-7-苯庚酸乙酯油状物一批量,再加入THF(四氢呋喃)200ml和2.5mol/L氢氧化钠水溶

液200ml的混合液,将该反应混合物于70ºC搅拌回流3h.冷却后加入异丙醚(IPE)200ml和饱和食盐水200ml,分出水层,水层用IPE65ml洗涤,用4mol/L盐酸酸化至pH3,乙酸乙酯500ml分3次提取,合并提取液,依次用水、盐水洗,干燥,浓缩(减压下)得4. 7-羟基-7-苯庚酸油状物42.2g,收率95%.

5. 塞曲司特的合成

在反应瓶中加入三甲基氢醌28.9g(190mmol)、4. 7-羟基-7-苯庚酸42.2g(190mmol)和甲苯570ml,在60ºC下20min内滴加三氟化硼乙醚配合物8.1g(57mmol),加毕,在相同的条件下搅拌2h.然后减压浓缩至干,将剩余物用THF300ml溶解,再加入1.5mol/LFeCl3溶液300ml(在室温下进行),混合物继续搅拌30min.减压浓缩,剩余物用乙酸乙酯500ml提取,提取液用盐水洗,干燥,将乙酸乙酯层通过硅胶(色谱用)100g过滤,再用乙酸乙酯300ml洗硅胶,合并乙酸乙酯液,减压浓缩至干,剩余物用乙醇重结晶,得到塞曲司特的橙黄色结晶49.0g,收率73%,回收母液中的塞曲司特可得8.4g,总共得57.4g,则收率为85.3%,mp128~129ºC.

塞曲司特海关

[ 海关编码 ]: 29309070