569-57-3 氯烯雌醚

氯烯雌醚

英文名称:chlorotrianisene
CAS:

569-57-3

分子式:C23H21ClO3
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氯烯雌醚简介

Chlorotrianisene (INN, USAN, BAN; brand names Tace, Estregur, Anisene, Clorotrisin, Merbentyl, Triagen, many others; also known as CTA; tri-p-anisylchloroethylene, TACE, or tris(p-methoxyphenyl)chloroethylene) is a synthetic, non-steroidal estrogen of the triphenylethylene group that was formerly used for the treatment of menopausal symptoms, estrogen deficiency, and prostate cancer before being discontinued. It was approved in the United States as TACE in 1952, and was introduced throughout Europe subsequently. CTA was the first estrogenic compound of the triphenylethylene series to be introduced.
CTA was derived from estrobin (DBE), a derivative of the very weakly estrogenic compound triphenylethylene (TPE), which in turn was derived from structural modification of diethylstilbestrol (DES). CTA is a relatively weak estrogen, with about one-eighth the potency of DES. However, it is highly lipophilic and is stored in fat tissue for prolonged periods of time, with its slow release from fat resulting in a very long duration of action. CTA itself is inactive; it behaves as a prodrug to a weak estrogen that is formed as a metabolite via degradation of CTA in the liver. As such, the potency of CTA is reduced if it is given parenterally instead of orally.
Although it is referred to as a weak estrogen and was used solely as an estrogen in clinical practice, CTA is actually a partial agonist of the estrogen receptor. As such, it is a selective estrogen receptor modulator (SERM), with predominantly estrogenic but also antiestrogenic effects, and was arguably the first SERM to ever be introduced. CTA can antagonize estradiol at the level of the hypothalamus, resulting in disinhibition of the hypothalamic-pituitary-gonadal axis and an increase in estrogen levels. Clomifene and tamoxifen were both derived from CTA via structural modification, and are much weaker partial agonists than CTA and hence much more antiestrogenic in comparison. As an example, chlorotrianisene produces gynecomastia in men, albeit reportedly to a lesser extent than other estrogens, while clomifene and tamoxifen do not and can actually be used to treat gynecomastia.

氯烯雌醚基本信息

中文名称 氯烯雌醚 英文名称 chlorotrianisene
中文别名

泰舒;

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英文别名

2-Chlor-1,1,2-tris-(4-methoxy-phenyl)-aethylen; Chlorotrianisine; 1-[1-chloro-2,2-bis(4-methoxyphenyl)ethenyl]-4-methoxybenzene; 1-chloro-1,2,2-tris(p-methoxyphenyl)ethene; Chlorotrianisene; Merbentul; TACE; chloro-tris-(4-methoxy-phenyl)-ethene; Tris-(4-methoxy-phenyl)-vinylchlorid; 1,1',1''-(1-chloro-1-ethenyl-2-ylidene)tris[4-methoxy-benzene]; Chlor-tris-(4-methoxy-phenyl)-aethen; Chloortrianisestrol; Chlorotrianizen; Chlortrianizen; Benzene, 1,1‘,1‘‘-(1-chloro-1-ethenyl-2-ylidene)tris[4-methoxy-; Chlorestrolo; Chlortrianisestrol; Chlortrianisen;

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CAS号 569-57-3 分子式 C23H21ClO3
分子量 380.86400 精确质量 380.11800
PSA 27.69000 LOGP 5.86780

氯烯雌醚编号系统

UNII 6V5034L121

氯烯雌醚物化性质

密度:
1.168g/cm3
沸点:
514.2ºC at 760mmHg
熔点:
114-116ºC
闪点:
164.1ºC
折射率:
1.591

安全信息

RTECS号:
KV0600000
WGK Germany:
3

生产方法及用途

生产方法

有多种合成路线,由对甲氧基苯乙酮经溴化、成盐、缩合、氯化而得。总收率14.5%;也可由茴香酸出发制备,总收率44.4%,但茴香酸原料价格较贵。以茴香醚为原料,经下列步骤制取泰舒,总收率为21.6%。
1.氯代对甲氧基苯乙酮的制备 茴香醚与氯乙酰氯反应得氯代对甲氧基苯乙酮。2.1,1,2-三(对甲氧苯基)乙烯的制备 溴代茴香醚与镁制得格氏试剂,与氯代对甲氧基苯乙酮反应得油状物继续与PTS反应得1,1,2-三(对甲氧苯基)乙烯。
3.泰舒的制备 1,1,2-三(对甲氧苯基)乙烯氯化得泰舒。

用途

雌激素类药,主要用于治疗前列腺肿大和妇女更年期综合症。

SDS 1.0 中文 展开
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1H NMR : Predict展开

核磁图谱 1H NMR : Predict

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氯烯雌醚
CAS号:569-57-3 分子式:C23H21ClO3 分子量:380.86400

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