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(E)-1-(4-HYDROXYPHENYL)-1-[4-(TRIMETHYLACETOXY)PHENYL]-2-PHENYLBUT-1-ENE is a complex organic compound characterized by its off-white solid appearance. It is an analogue of tamoxifen, a well-known drug used in the treatment of breast cancer, and possesses anti-estrogenic properties.

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  • (E)-1-(4-HYDROXYPHENYL)-1-[4-(TRIMETHYLACETOXY)PHENYL]-2-PHENYLBUT-1-ENE

    Cas No: 177748-17-3

  • USD $ 1.9-2.9 / Gram

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  • 177748-17-3 Structure
  • Basic information

    1. Product Name: (E)-1-(4-HYDROXYPHENYL)-1-[4-(TRIMETHYLACETOXY)PHENYL]-2-PHENYLBUT-1-ENE
    2. Synonyms: (E)-1-(4-HYDROXYPHENYL)-1-[4-(TRIMETHYLACETOXY)PHENYL]-2-PHENYLBUT-1-ENE;(E)-2,2-DiMethyl-propanoic Acid 4-[1-(4-hydroxyphenyl)-2-phenyl-1-butenyl]phenyl Ester;(E)-4-(1-(4-hydroxyphenyl)-2-phenylbut-1-en-1-yl)phenyl pivalate;(E)-4-(1-(4-hydroxyphenyl)-2-phenylbut-1-en-1-yl)phenyl pivalate(WXC07047)
    3. CAS NO:177748-17-3
    4. Molecular Formula: C27H28O3
    5. Molecular Weight: 400.51
    6. EINECS: N/A
    7. Product Categories: Drug Analogues;Intermediates & Fine Chemicals;Pharmaceuticals;Steroids
    8. Mol File: 177748-17-3.mol
  • Chemical Properties

    1. Melting Point: 171-173°C
    2. Boiling Point: 509.3±40.0 °C(Predicted)
    3. Flash Point: N/A
    4. Appearance: /
    5. Density: 1.109±0.06 g/cm3(Predicted)
    6. Refractive Index: N/A
    7. Storage Temp.: N/A
    8. Solubility: Dichloromethane, Ethyl Acetate, Methanol
    9. PKA: 10.25±0.15(Predicted)
    10. CAS DataBase Reference: (E)-1-(4-HYDROXYPHENYL)-1-[4-(TRIMETHYLACETOXY)PHENYL]-2-PHENYLBUT-1-ENE(CAS DataBase Reference)
    11. NIST Chemistry Reference: (E)-1-(4-HYDROXYPHENYL)-1-[4-(TRIMETHYLACETOXY)PHENYL]-2-PHENYLBUT-1-ENE(177748-17-3)
    12. EPA Substance Registry System: (E)-1-(4-HYDROXYPHENYL)-1-[4-(TRIMETHYLACETOXY)PHENYL]-2-PHENYLBUT-1-ENE(177748-17-3)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 177748-17-3(Hazardous Substances Data)

177748-17-3 Usage

Uses

Used in Pharmaceutical Industry:
(E)-1-(4-HYDROXYPHENYL)-1-[4-(TRIMETHYLACETOXY)PHENYL]-2-PHENYLBUT-1-ENE is used as a pharmaceutical agent for its anti-estrogenic properties. It serves as a tamoxifen analogue, which can be beneficial in the treatment of estrogen receptor-positive breast cancer. The compound's ability to modulate estrogen signaling pathways may contribute to its therapeutic potential in this application.
Used in Research and Development:
In the field of research and development, (E)-1-(4-HYDROXYPHENYL)-1-[4-(TRIMETHYLACETOXY)PHENYL]-2-PHENYLBUT-1-ENE can be utilized as a starting material or a reference compound for the synthesis of new drugs with potential applications in various therapeutic areas. Its structural similarity to tamoxifen makes it a valuable tool for studying the mechanisms of estrogen signaling and the development of novel anti-estrogenic agents.
Used in Drug Delivery Systems:
Similar to gallotannin, (E)-1-(4-HYDROXYPHENYL)-1-[4-(TRIMETHYLACETOXY)PHENYL]-2-PHENYLBUT-1-ENE could potentially be incorporated into drug delivery systems to enhance its bioavailability, delivery, and therapeutic outcomes. The development of novel drug delivery systems, such as organic and metallic nanoparticles, could improve the compound's efficacy and reduce potential side effects.

Check Digit Verification of cas no

The CAS Registry Mumber 177748-17-3 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,7,7,7,4 and 8 respectively; the second part has 2 digits, 1 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 177748-17:
(8*1)+(7*7)+(6*7)+(5*7)+(4*4)+(3*8)+(2*1)+(1*7)=183
183 % 10 = 3
So 177748-17-3 is a valid CAS Registry Number.

177748-17-3Relevant articles and documents

Gefitinib-Tamoxifen Hybrid Ligands as Potent Agents against Triple-Negative Breast Cancer

Abdelmalek, Carine M.,Hu, Zexi,Kronenberger, Thales,Küblbeck, Jenni,Kinnen, Franziska J. M.,Hesse, Salma S.,Malik, Afsin,Kudolo, Mark,Niess, Raimund,Gehringer, Matthias,Zender, Lars,Witt-Enderby, Paula A.,Zlotos, Darius P.,Laufer, Stefan A.

, p. 4616 - 4632 (2022/04/07)

Anticancer drug conjugates may benefit from simultaneous action at two targets potentially overcoming the drawbacks of current cancer treatment, such as insufficient efficacy, high toxicity, and development of resistance. Compared to a combination of two single-target drugs, they may offer an advantage of pharmacokinetic simplicity and fewer drug-drug interactions. Here, we report a series of compounds connecting tamoxifen or endoxifen with the EGFR-inhibitor gefitinib via a covalent linkage. These hybrid ligands retain both ER antagonist activity and EGFR inhibition. The most potent analogues exhibited single-digit nanomolar activities at both targets. The amide-linked endoxifen-gefitinib drug conjugates 17b and 17c demonstrated the most favorable anti-cancer profile in cellular viability assays on MCF7, MDA-MB-231, MDA-MB-468, and BT-549 breast cancer cells. Most importantly, in TNBC cells 17b and 17c displayed nanomolar IC50-values (380 nM - 970 nM) and were superior in their anti-cancer activity compared to their control compounds and combinations thereof.

NOVEL COMPOUNDS HAVING ESTROGEN RECEPTOR ALPHA DEGRADATION ACTIVITY AND USES THEREOF

-

, (2020/06/08)

The present disclosure relates to novel compounds having estrogen receptor alpha degradation activity, pharmaceutical compositions containing such compounds, and their use in prevention and treatment of cancer and related diseases and conditions.

Rational design of ERα targeting hypoxia turn-on fluorescent probes with antiproliferative activity for breast cancer

Dong, Chune,Hu, Zhiye,Ma, Xiaoyu,Meng, Qiuyu,Xie, Baohua,Zhou, Fuling,Zhou, Hai-Bing

, p. 10493 - 10496 (2020/10/02)

The overexpression of estrogen receptor (ER) α is not only closely related to the development of ER+ breast cancer, but is also an important biomarker for clinical diagnosis and treatment. Herein, we report several ERα targeting hypoxia turn-on fluorescent probes with antitumor activity for breast cancer cells. Among them, probes 3 and 5 displayed good ERα targeting ability and favorable hypoxia turn-on response in MCF-7 cells. Moreover, the probes 3 and 5 exhibited good antiproliferative activity towards MCF-7 cells (IC50 = 8.5 μM, 10.3 μM) and a much lower cytotoxicity to normal cells compared with the positive control. It is expected that these novel fluorescent probes may provide useful tools for the theranostics of ER+ breast cancer.

ANTI-CANCER NUCLEAR HORMONE RECEPTOR-TARGETING COMPOUNDS

-

, (2019/12/04)

The disclosure relates to anti-cancer compounds derived from nuclear steroid receptor binders, to products containing the same, as well as to methods of their use and preparation.

A multi-gram-scale stereoselective synthesis of Z-endoxifen

Milroy, Lech-Gustav,Koning, Bartjan,Scheppingen, Daphne S.V.,Jager, Nynke G.L.,Beijnen, Jos H.,Koek, Jan,Brunsveld, Luc

, p. 1352 - 1356 (2018/03/21)

Z-Endoxifen is widely regarded as the most active metabolite of tamoxifen, and has recently demonstrated a 26.3% clinical benefit in a phase I clinical trial to treat metastatic breast cancer after the failure of standard endocrine therapy. Future pharmac

Synthesis of mixed (E, Z)-, (E)-, and (Z)-norendoxifen with dual aromatase inhibitory and estrogen receptor modulatory activities

Lv, Wei,Liu, Jinzhong,Lu, Deshun,Flockhart, David A.,Cushman, Mark

, p. 4611 - 4618 (2013/07/19)

The first synthesis of the tamoxifen metabolite norendoxifen is reported. This included syntheses of (E)-norendoxifen, (Z)-norendoxifen, and (E,Z)-norendoxifen isomers. (Z)-Norendoxifen displayed affinity for aromatase (Ki 442 nM), estrogen receptor-α (EC50 17 nM), and estrogen receptor-β (EC50 27.5 nM), while the corresponding values for (E)-norendoxifen were aromatase (Ki 48 nM), estrogen receptor-α (EC50 58.7 nM), and estrogen receptor-β (EC50 78.5 nM). Docking and energy minimization studies were performed with (E)-norendoxifen on aromatase, and the results provide a foundation for structure-based drug design. The oral pharmacokinetic parameters for (E,Z)-norendoxifen were determined in mice, and (Z)-norendoxifen was found to result in significantly higher plasma concentrations and exposures (AUC values) than (E)-norendoxifen. The affinities of both isomers for aromatase and the estrogen receptors, as well as the pharmacokinetic results, support the further development of norendoxifen and its analogues for breast cancer treatment.

Synthesis and structure-activity relationships of ferrocenyl tamoxifen derivatives with modifed side chains

Nguyen, Anh,Top, Siden,Pigeon, Pascal,Vessieres, Anne,Hillard, Elizabeth A.,Plamont, Marie-Aude,Huche, Michel,Rigamonti, Clara,Jaouen, Gerard

scheme or table, p. 684 - 696 (2009/07/25)

We report here the synthesis and cell-proliferation properties of derivatives of the breast cancer drug tamoxifen, in which the -O(CH 2)2N-(CH3)2 side chain, responsible for the drug's antiestrogenic properties,

Identification of new triarylethylene oxyalkanoic acid analogues as bone selective estrogen mimetics

Rubin, Valeria N,Ruenitz, Peter C,Boudinot,Boyd, Jason L

, p. 1579 - 1587 (2007/10/03)

Previously, the estrogen receptor (ER) ligand 4-[1-(p-hydroxyphenyl)-2-phenylethyl]phenoxyacetic acid (5) was found to have differential bone loss suppressive effects in the ovariectomized (OVX) rat approaching those of selective ER modulators (SERMs) suc

Synthesis and Sulfatase Inhibitory Activities of (E)- and (Z)-4-Hydroxytamoxifen Sulfamates

Chu, Guo-Hua,Peters, Amy,Selcer, Kyle W.,Li, Pui-Kai

, p. 141 - 144 (2007/10/03)

We report the development of (E)- and (Z)-4-hydroxytamoxifen sulfamates as estrone sulfatase inhibitors, potential therapeutic agents for the treatment of breast cancer. Both compounds competitively inhibit estrone sulfatase isolated from rat liver with apparent Ki of 35.9 μM for (E)-4-hydroxytamoxifen sulfamate and an apparent Ki of >500 μM for the (Z) isomer.

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