362-07-2 Usage
Description
2-Methoxyestradiol, also known as 2-METHOXYESTRADIOL, is a 17beta-hydroxy steroid derived from 17beta-estradiol by methoxylation at the C-2 position. It is an off-white solid and is devoid of estrogenic activity. This natural metabolite has been found to inhibit cell proliferation, angiogenesis, and regulate microtubule assembly, making it a potential candidate for various applications in the pharmaceutical and medical industries.
Uses
Used in Pharmaceutical Industry:
2-Methoxyestradiol is used as a tubulin polymerization inhibitor for its ability to bind to the colchicine binding site of tubulin, functioning as a natural regulator of microtubule assembly and function. This property makes it a promising agent for targeting cancer cells and inhibiting their growth.
Used in Cancer Treatment:
2-Methoxyestradiol is used as an anticancer agent due to its ability to inhibit cell proliferation and angiogenesis. It has been suggested to be effective against various types of cancer by disrupting the microtubule assembly and blocking HIF-1α nuclear accumulation and HIF-transcriptional activity.
Used in Drug Development:
2-Methoxyestradiol is used as a lead compound in the development of new drugs targeting microtubule dynamics and HIF-1 activity, which are essential for cancer cell survival and progression.
Used in Research:
2-Methoxyestradiol serves as a valuable tool in research for understanding the role of microtubules in cell division and the potential of targeting these structures for therapeutic purposes.
Biological Activity
Apoptotic, antiproliferative and antiangiogenic agent, in vitro and in vivo ; acts via an estrogen receptor-independent mechanism. Induces p53-induced apoptosis via two pathways: activation of p38 and NF- κ B; and activation of JNK and AP-1 leading to Bcl-2 phosphorylation. Also upregulates death receptor 5 and binds to tubulin, inhibiting its assembly.
Check Digit Verification of cas no
The CAS Registry Mumber 362-07-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 3,6 and 2 respectively; the second part has 2 digits, 0 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 362-07:
(5*3)+(4*6)+(3*2)+(2*0)+(1*7)=52
52 % 10 = 2
So 362-07-2 is a valid CAS Registry Number.
InChI:InChI=1/C19H26O3/c1-19-8-7-12-13(15(19)5-6-18(19)21)4-3-11-9-16(20)17(22-2)10-14(11)12/h9-10,12-13,15,18,20-21H,3-8H2,1-2H3/t12?,13-,15?,18+,19+/m1/s1
362-07-2Relevant articles and documents
Synthesis of 2-Methoxy- and 4-Methoxy-Estrogens with Halogen-Methoxy Exchange Reaction
Numazawa, Mitsuteri,Ogura, Yuko,Kimura, Katsuhiko,Nagaoka, Masao
, p. 3701 - 3715 (2007/10/02)
Synthesis of 2-methoxy- and 4-methoxy-estrone (6) and (9), 2-methoxy- and 4-methoxy-estradiol (15) and (18), and 2-methoxy- and 4-methoxy-estratriol (24) and (27) are described.Catalytic hydrogenation over Pd/C of 2,4-dibromo or 2,4-diiodo estrogens gave regioselectively the corresponding 4-halogeno derivatives in excellent yields.Reaction of 2-iodo or 4-iodo estradiol and 2-iodo or 4-iodo estriol with NaOCH3 in MeOH and dimethylformamide (DMF) in the presence of CuCl2 gave in an excellent yield and in a good yield, while (6) and (9) were also similarly obtained by the reaction with pyridine instead of DMF.
Efficient Synthesis of 2-Methoxy- and 4-Methoxy-estrogens
Numazawa, Mitsuteru,Ogura, Yuko
, p. 533 - 534 (2007/10/02)
2-Methoxy- and 4-methoxy-estrogens are easily prepared from the corresponding 2-iodo or 4-bromo derivatives in high yields by a halogen-methoxy group exchange reaction using sodium methoxide-copper(II) chloride.
