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Levcromakalim, also known as BRL 38167, is a potassium channel activator and vasorelaxant. It is a member of the class of drugs known as potassium channel openers and is used in the management of hypertension in diabetes mellitus. Levcromakalim works by activating potassium channels in smooth muscle cells, leading to relaxation of the blood vessels and a reduction in blood pressure.

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  • Levcromakalim,(3s,4r)-3,4-dihydro-3-hydroxy-2,2-dimethyl-4-(2-oxo-1-pyrrolidinyl)-2h-1-benzopyran-6-carbonitrile

    Cas No: 94535-50-9

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  • 1 Kilogram

  • 100 Kilogram/Week

  • Career Henan Chemical Co
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  • 94535-50-9 Structure
  • Basic information

    1. Product Name: LEVCROMAKALIM
    2. Synonyms: LEVCROMAKALIM;(3S,4R)-3,4-DIHYDRO-3-HYDROXY-2,2-DIMETHYL-4-(2-OXO-1-PYRROLIDINYL)-2H-1-BENZOPYRAN-6-CARBONITRILE;(3s-trans)-yrrolidinyl);2h-1-benzopyran-6-carbonitrile,3,4-dihydro-3-hydroxy-2,2-dimethyl-4-(2-oxo-1-p;brl38227;lemakalim;levcromakelim;(3S,4R)-3β-Hydroxy-4-(2-oxopyrrolizino)-2,2-dimethyl-3,4-dihydro-6-cyano-2H-1-benzopyran
    3. CAS NO:94535-50-9
    4. Molecular Formula: C16H18N2O3
    5. Molecular Weight: 286.33
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 94535-50-9.mol
  • Chemical Properties

    1. Melting Point: 242-244°
    2. Boiling Point: 482.3°Cat760mmHg
    3. Flash Point: 245.5°C
    4. Appearance: /solid
    5. Density: 1.31g/cm3
    6. Refractive Index: N/A
    7. Storage Temp.: Store at RT
    8. Solubility: DMSO: ≤10 mM, soluble
    9. PKA: 13.18±0.60(Predicted)
    10. CAS DataBase Reference: LEVCROMAKALIM(CAS DataBase Reference)
    11. NIST Chemistry Reference: LEVCROMAKALIM(94535-50-9)
    12. EPA Substance Registry System: LEVCROMAKALIM(94535-50-9)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: 22-24/25
    4. WGK Germany: 3
    5. RTECS: DJ2177500
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 94535-50-9(Hazardous Substances Data)

94535-50-9 Usage

Uses

Used in Pharmaceutical Industry:
Levcromakalim is used as an anti-asthmatic agent for the treatment of asthma. It helps to relax the smooth muscles in the airways, improving lung function and reducing symptoms of asthma.
Used in Pharmaceutical Industry:
Levcromakalim is used as an antihypertensive agent for the management of hypertension in diabetes mellitus. It helps to lower blood pressure by relaxing the blood vessels, reducing the workload on the heart and improving blood flow.
Used in Pharmaceutical Industry:
Levcromakalim is used as a vasorelaxant for the treatment of various cardiovascular conditions. Its ability to relax blood vessels can help to improve blood flow and reduce the risk of heart disease and stroke.

Biological Activity

Active enantiomer of the prototypical K ATP channel opener cromakalim (trans-3,4-dihydro-3-hydroxy-2,2-dimethyl-4-(2-oxo-1-pyrrolidinyl)-2H-1-benzopyran-6-carbonitrile ). Hypotensive and airways relaxant. IC 50 = 490 nM in guinea pig trachea.

Check Digit Verification of cas no

The CAS Registry Mumber 94535-50-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 9,4,5,3 and 5 respectively; the second part has 2 digits, 5 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 94535-50:
(7*9)+(6*4)+(5*5)+(4*3)+(3*5)+(2*5)+(1*0)=149
149 % 10 = 9
So 94535-50-9 is a valid CAS Registry Number.

94535-50-9SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name Levcromakalim,(3S,4R)-3,4-dihydro-3-hydroxy-2,2-dimethyl-4-(2-oxo-1-pyrrolidinyl)-2H-1-benzopyran-6-carbonitrile

1.2 Other means of identification

Product number -
Other names levcromakelim

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:94535-50-9 SDS

94535-50-9Downstream Products

94535-50-9Relevant articles and documents

CONTROLLED-DELIVERY CROMAKALIM PRODRUGS

-

Page/Page column 167-169, (2021/06/22)

The present invention provides cromakalim prodrugs, compositions, and their use for the modulation of ATP-sensitive potassium (KATP) channels for therapeutic purposes.

Total synthesis of chromanol 293B and cromakalim via stereoselective amination of chiral benzylic ethers

Ma, Sang-Ho,Kim, Yeon Su,Jung, Jun Min,Boggu, Pulla Reddy,Kim, Seung Chan,Kim, In Su,Jung, Young Hoon

supporting information, (2020/01/21)

Stereoselective benzylic amination reaction is important for their further application as pharmaceuticals and agrochemicals, and other chemical entities. Herein, we describe the diastereoselective amination of 1,2-anti-dialkoxychromane on chromane framewo

Chiral Manganese Aminopyridine Complexes: the Versatile Catalysts of Chemo- and Stereoselective Oxidations with H2O2

Ottenbacher, Roman V.,Talsi, Evgenii P.,Bryliakov, Konstantin P.

, p. 78 - 90 (2017/10/06)

In the last decade, manganese(II) complexes with N-donor tetradentate aminopyridine ligands emerged as efficient catalysts of enantioselective epoxidation of olefins and direct selective oxidation of C?H groups in complex organic molecules, with environmentally benign oxidant hydrogen peroxide. In this personal account, we summarize the progress of these catalysts with regard to ligands design, structure-reactivity correlations, evaluation of the substrate scope, as well as mechanistic studies, shedding light on the nature of active sites and the mechanisms of selective oxygenations. Several practically promising catalytic syntheses with the aid of Mn aminopyridine catalysts are exemplified.

Asymmetric epoxidation of alkenes catalyzed by a porphyrin-inspired manganese complex

Dai, Wen,Li, Jun,Li, Guosong,Yang, Hua,Wang, Lianyue,Gao, Shuang

, p. 4138 - 4141 (2013/09/12)

A novel strategy for catalytic asymmetric epoxidation of a wide variety of olefins by a porphyrin-inspired chiral manganese complex using H 2O2 as a terminal oxidant in excellent yield with up to greater than 99% ee has been successfully developed.

Immobilized dimeric chiral Mn(III) salen complex on short channel ordered mesoporous silica as an effective catalyst for the epoxidation of non-functionalized alkenes

Roy, Tamal,Kureshy, Rukhsana I.,Khan, Noor-Ul H.,Abdi, Sayed H.R.,Sadhukhan, Arghya,Bajaj, Hari C.

experimental part, p. 6314 - 6322 (2012/08/28)

Chiral dimeric Mn(III) salen complex with 1R, 2R-(-)-diaminocyclohexane collar was immobilized on short channel large pore sized silica through a long linker of {(CH2)3-NH-melamine-piperazine} to investigate its performance in enanti

COMPOSITIONS AND METHODS FOR CYCLOFRUCTANS AS SEPARATION AGENTS

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Page/Page column 45-49; 55, (2010/12/31)

The present invention relates to derivatized cyclofructan compounds, compositions comprising derivatized cyclofructan compounds, and methods of using compositions comprising derivatized cyclofructan compounds for chromatographic separations of chemical species, including enantiomers. Said compositions may comprise a solid support and/or polymers comprising derivatized cyclofructan compounds.

Development of new HPLC chiral stationary phases based on native and derivatized cyclofructans

Sun, Ping,Wang, Chunlei,Breitbach, Zachary S.,Zhang, Ying,Armstrong, Daniel W.

experimental part, p. 10215 - 10226 (2010/05/01)

An unusual class of chiral selectors, cyclofructans, is introduced for the first time as bonded chiral stationary phases. Compared to native cyclofructans (CFs), which have rather limited capabilities as chiral selectors, aliphatic-and aromatic-functionalized CF6s possess unique and very different enantiomeric selectivities. Indeed, they are shown to separate a very broad range of racemic compounds. In particular, aliphatic-derivatized CF6s with a low substitution degree baseline separate all tested chiral primary amines. It appears that partial derivatization on the CF6 molecule disrupts the molecular internal hydrogen bonding, thereby making the core of the molecule more accessible. In contrast, highly aromaticfunctionalized CF6 stationary phases lose most of the enantioselective capabilities toward primary amines, however they gain broad selectivity for most other types of analytes. This class of stationary phases also demonstrates high "loadability" and therefore has great potential for preparative separations. The variations in enantiomeric selectivity often can be correlated with distinct structural features of the selector. The separations occur predominantly in the presence of organic solvents.

Asymmetric epoxidation of cis-alkenes mediated by iminium salts: Highly enantioselective synthesis of levcromakalim

Page, Philip C. Bulman,Buckley, Benjamin R.,Heaney, Harry,Blacker, A. John

, p. 375 - 377 (2007/10/03)

(Chemical Equation Presented) A range of cis-substituted olefins has been epoxidized with a new dihydroisoquinolinium salt catalyst, using tetraphenylphosphonium monoperoxysulfate as the stoichiometric oxidant, giving ee's of up to 97%. The reaction has been used as the key step in an enantioselective synthesis of the antihypertensive agent levcromakalim.

Enantiomerically pure epoxychromans via asymmetric catalysis

Lee,Muci,Jacobsen

, p. 5055 - 5058 (2007/10/02)

A practical and highly effective process for the asymmetric epoxidation of several 2,2-dimethylchromene derivatives is reported. Catalysis by Mn(salen) complex 4 in all cases affords epoxychromans with >90% ee, and this method has been applied to the synthesis of two recently developed antihypertensive agents in enantiomerically pure form.

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