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(10R,13S)-17-chloro-16-formyl-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate is a complex organic compound with a steroidal structure. It features a chloro group, a formyl group, and an acetate functional group at specific positions on the steroid backbone, along with two methyl groups at positions 10 and 13. This chemical is characterized by its unique stereochemistry and functional groups, which may confer biological activity and potential applications in pharmaceutical research or other fields related to steroids and hormonal regulation.

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  • (10R,13S)-17-Chloro-16-formyl-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate

    Cas No: 1865-56-1

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  • (10R,13S)-17-Chloro-16-formyl-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate

    Cas No: 1865-56-1

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  • (10R,13S)-17-chloro-16-forMyl- 10,13-diMethyl-2,3,4,7,8,9,10, 11,12,13,14,15-dodecahydro- 1H-cyclopenta[a]phenanthren-3- yl acetate

    Cas No: 1865-56-1

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  • 1865-56-1 Structure
  • Basic information

    1. Product Name: (10R,13S)-17-chloro-16-forMyl- 10,13-diMethyl-2,3,4,7,8,9,10, 11,12,13,14,15-dodecahydro- 1H-cyclopenta[a]phenanthren-3- yl acetate
    2. Synonyms: (10R,13S)-17-chloro-16-forMyl- 10,13-diMethyl-2,3,4,7,8,9,10, 11,12,13,14,15-dodecahydro- 1H-cyclopenta[a]phenanthren-3- yl acetate;3-Acetoxy-17-chloro-16-forMylandrosta-5,16-dieneo;4,7,8,9,10, 11,12,13,14,15-dodecahydro- 1H-cyclopenta[a]phenanthren-3- yl acetate;(3beta)-3-(Acetyloxy)-17-chloroandrosta-5,16-diene-16-carboxaldehyde;(3S,8R,9S,10R,13S,14S)-17-chloro-16-forMyl-10,13-diMethyl-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate;(10R,13S)-17-chloro-16-forMyl- 10,13-diMethyl-2,3,4,7,8,9,10, 11,12,13,14,15-dodecahydro- 1H-;(3S,8R,9S,10R,13S)-17-chloro-16-formyl-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate
    3. CAS NO:1865-56-1
    4. Molecular Formula: C22H29ClO3
    5. Molecular Weight: 377
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 1865-56-1.mol
  • Chemical Properties

    1. Melting Point: 180-182℃
    2. Boiling Point: N/A
    3. Flash Point: N/A
    4. Appearance: /
    5. Density: 1.19
    6. Refractive Index: N/A
    7. Storage Temp.: N/A
    8. Solubility: N/A
    9. CAS DataBase Reference: (10R,13S)-17-chloro-16-forMyl- 10,13-diMethyl-2,3,4,7,8,9,10, 11,12,13,14,15-dodecahydro- 1H-cyclopenta[a]phenanthren-3- yl acetate(CAS DataBase Reference)
    10. NIST Chemistry Reference: (10R,13S)-17-chloro-16-forMyl- 10,13-diMethyl-2,3,4,7,8,9,10, 11,12,13,14,15-dodecahydro- 1H-cyclopenta[a]phenanthren-3- yl acetate(1865-56-1)
    11. EPA Substance Registry System: (10R,13S)-17-chloro-16-forMyl- 10,13-diMethyl-2,3,4,7,8,9,10, 11,12,13,14,15-dodecahydro- 1H-cyclopenta[a]phenanthren-3- yl acetate(1865-56-1)
  • 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: 1865-56-1(Hazardous Substances Data)

1865-56-1 Usage

Uses

Used in Pharmaceutical Research:
(10R,13S)-17-chloro-16-formyl-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate is used as a research compound in pharmaceutical research for its potential biological activity. Its steroidal structure and functional groups may allow it to interact with various biological targets, such as receptors or enzymes, and modulate their functions.
Used in Hormonal Regulation Studies:
Due to its steroidal structure, (10R,13S)-17-chloro-16-formyl-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate may be used in studies related to hormonal regulation. It could potentially serve as a modulator or antagonist of hormonal pathways, providing insights into the mechanisms of hormone action and the development of new therapeutic agents.
Used in Drug Design and Development:
The unique functional groups and stereochemistry of (10R,13S)-17-chloro-16-formyl-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate make it a valuable starting point for drug design and development. Researchers can use this compound as a template to create new molecules with improved pharmacological properties, such as increased potency, selectivity, or reduced side effects.
Used in Chemical Synthesis:
(10R,13S)-17-chloro-16-formyl-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate can also be used as a synthetic intermediate or building block in the preparation of other complex organic compounds. Its versatile functional groups and unique structure make it a valuable asset in the synthesis of novel molecules with potential applications in various fields, such as materials science, agrochemistry, or environmental chemistry.

Check Digit Verification of cas no

The CAS Registry Mumber 1865-56-1 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,8,6 and 5 respectively; the second part has 2 digits, 5 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 1865-56:
(6*1)+(5*8)+(4*6)+(3*5)+(2*5)+(1*6)=101
101 % 10 = 1
So 1865-56-1 is a valid CAS Registry Number.

1865-56-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name [(3S,10R,13S)-17-chloro-16-formyl-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate

1.2 Other means of identification

Product number -
Other names CX1340

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:1865-56-1 SDS

1865-56-1Relevant articles and documents

Heterocyclic steroids: Synthesis of androsteno[17,16-d]pyrazoles and androsteno[17,16-e]pyrimidines

Siddiqui,Rao,Maimirani,Siddiqui

, p. 353 - 354 (1995)

The Vilsmeier-Haack reaction of 3β-acetoxyandost-5-en-17-one (1) with phosphorous oxychloride and dimethylformamide gave 3β-acetoxy-17-chloro-16-formylandrosta-5,16-diene (2). Reaction of 2 with hydrazine and phenylhydrazine provided substituted 5-androst

Access to steroidal pyridazines via modified thiohydrazides

Volkova,Antonov,Komkov,Scherbakov,Shashkov,Menchikov,Chernoburova,Zavarzin

, p. 42863 - 42868 (2016)

An approach to steroids annulated with pyridazines via cascade imination/electrocyclization of chlorovinyl aldehydes with oxamic acid thiohydrazides is disclosed. A mechanistic rationalization was performed using real-time 1H NMR spectroscopy a

Discovery and development of galeterone (TOK-001 or VN/124-1) for the treatment of all stages of prostate cancer

Njar, Vincent C. O.,Brodie, Angela M. H.

, p. 2077 - 2087 (2015)

In our effort to discover potent and specific inhibitors of 17α-hydroxylase/17,20-lyase (CYP17), the key enzyme which catalyzes the biosynthesis of androgens from progestins, 3β-(hydroxy)-17-(1H-benzimidazole-1-yl)androsta-5,16-diene (Galeterone or TOK-001, formerly called VN/124-1) was identified as a selective development candidate which modulates multiple targets in the androgen receptor (AR) signaling pathway. This drug annotation summarizes the mechanisms of action, scientific rationale, medicinal chemistry, pharmacokinetic properties, and human efficacy data for galeterone, which has successfully completed phase II clinical development in men with castration resistant (advanced) prostate cancer (CRPC). Phase III clinical studies in CRPC patients are scheduled to begin in early 2015.

Synthesis of Heterocyclic-Substituted Novel Hydroxysteroids with Regioselective and Stereoselective Reactions

Kolo, Abubakar Mohammed,?pek, Emine,?apan, ?rfan,Servi, Süleyman

, p. 492 - 497 (2018)

Polyhydroxy steroids bearing the 3β,5α,6β-trihydroxy pattern were synthesized from different heterocyclic-substituted unsaturated steroid by an easy and simple method with high yields. The endocyclic double bond of thiophene-substituted and quinoline-substituted steroids were converted to the trans-diaxial diol by the regioselective and stereoselective reactions with m-chloroperoxybenzoic acid in the basic medium.

Novel steride androgen receptor antagonist, preparation method and medical application thereof

-

Paragraph 0016; 0018; 0019; 0021; 0022; 0024; 0054-0056, (2018/04/21)

The invention relates to the field of medicinal chemistry, in particular to a series of steride androgen receptor antagonist, and a preparation method and medical application thereof, and particularlyrelates to a medicine for treating androgen receptor related diseases, such as cell proliferation depending on androgens, hirsutism, acnes and androgen alopecia. The general molecular formula of thecompound is shown as follows, and groups in the formula are specified in the specification.

PROCESS FOR THE PREPARATION OF GALETERONE

-

Page/Page column 11-12, (2018/01/17)

A process for the synthesis of 3β-hydroxy-17-(1H-benzimidazol-1-yl)androsta-5,16-diene is described, a compound also known as Galeterone and used in the treatment of prostate cancer, having the formula (I) given below.

Efficient synthesis of 4- And 5-substituted 2-aminopyrimidines by coupling of β-Chlorovinyl Aldehydes and Guanidines

Komendantova, Anna S.,Komkov, Alexander V.,Volkova, Yulia A.,Zavarzin, Igor V.

supporting information, p. 4247 - 4254 (2018/08/24)

A general, practical, and simple synthesis of functionalized 2-aminopyrimidines starting from β-chlorovinyl aldehydes and amidines is reported. In the presence of potassium carbonate, various ketones have been efficiently transformed into the pyrimidine derivatives by a two-step sequence involving the Vilsmeier-Haack reaction followed by a condensation reaction with guanidines. The protocol is distinguished by operational simplicity, inexpensive reagents, and functional-group tolerance. In many cases, pure solid products can be obtained in high to excellent yields without using column chromatography. The synthetic value of the method was demonstrated by the efficient synthesis of steroidal pyrimidines and a precursor of the antitumor agents Imatinib and Mocetinostat.

Novel dehydroepiandrosterone benzimidazolyl derivatives as 5α-reductase isozymes inhibitors

Arellano, Yazmín,Bratoeff, Eugene,Segura, Tania,Mendoza, Maria Eugenia,Sánchez-Márquez, Araceli,Medina, Yesica,Heuze, Yvonne,Soriano, Juan,Cabeza, Marisa

, p. 908 - 914 (2016/10/09)

5α-R isozymes (types 1 and 2) play an important role in prostate gland development because they are responsible for intraprostatic dihydrotestosterone (DHT) levels when the physiological serum testosterone (T) concentration is low. In this study, we synthesized seven novel dehydroepiandrosterone derivatives with benzimidazol moiety at C-17, and determined their effect on the activity of 5α-reductase types 1 and 2. The derivatives with an aliphatic ester at C-3 of the dehydroepiandrosterone scaffold induced specific inhibition of 5α-R1 activity, whereas those with a cycloaliphatic ester (cyclopropyl, cyclobutyl, or cyclopentyl ring) or an alcohol group at C-3 inhibited the activity of both isozymes. Derivatives with a cyclohexyl or cycloheptyl ester at C-3 showed no inhibitory activity. In pharmacological experiments, derivatives with esters having an alcohol or the aliphatic group or one of the three smaller cycloaliphatic rings at C-3 decreased the diameter of male hamster flank organs, with the cyclobutyl and cyclopentyl esters exhibiting higher effect. With exception of the cyclobutyl and cyclopentyl esters, these compounds reduced the weight of the prostate and seminal vesicles.

Synthesis and biological evaluation of esters of 16-formyl-17-methoxy-dehydroepiandrosterone derivatives as inhibitors of 5α-reductase type 2

Sánchez-Márquez, Araceli,Arellano, Yazmín,Bratoeff, Eugene,Heuze, Yvonne,Córdova, Karen,Nieves, Gladys,Soriano, Juan,Cabeza, Marisa

, p. 1170 - 1176 (2016/10/09)

In this study, we investigated the in vitro effect of 16-formyl-17-methoxy dehydroepiandrosterone derivatives on the activity of 5α-reductase type 2 (5α-R2) obtained from human prostate. The activity of different concentrations of these derivatives was de

Biological activity of pyrazole and imidazole-dehydroepiandrosterone derivatives on the activity of 17 β-hydroxysteroid dehydrogenase

Cabeza, Marisa,Posada, Alejandro,Snchez-Mrquez, Araceli,Heuze, Yvonne,Moreno, Isabel,Soriano, Juan,Garrido, Mariana,Corts, Francisco,Bratoeff, Eugene

, p. 53 - 62 (2016/01/12)

The enzyme type 5 17β-hydroxysteroid dehydrogenase 5 (17β-HSD5) catalyzes the transformation of androstenedione (4-dione) to testosterone (T) in the prostate. This metabolic pathway remains active in cancer patients receiving androgen deprivation therapy.

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