CN106038551A - Application of composition of Schiglautone A derivatives in preparation of low-erythrocyte anemia preventive drugs - Google Patents
Application of composition of Schiglautone A derivatives in preparation of low-erythrocyte anemia preventive drugs Download PDFInfo
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4184—1,3-Diazoles condensed with carbocyclic rings, e.g. benzimidazoles
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
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Abstract
The invention relates to the field of organic synthesis and medicinal chemistry, in particular to a composition, a preparation of the composition and application of the composition in the preparation of low-erythrocyte anemia resisting drugs. The invention discloses a composition and a preparation method thereof. Pharmacological experiments show that the composition of the invention can resist low-erythrocyte anemia and is worthy of the development of low-erythrocyte anemia resisting drugs.
Description
Technical field
The present invention relates to organic synthesis and medicinal chemistry art, be specifically related to compositions, preparation method and its usage.
Background technology
Based on different clinical characters, anemia has different classification.As: divide acute and chronic anemia by anemia tempo；Press
Bone marrow red system proliferative conditions divides hyperplastic anemia (such as hemolytic anemia, iron deficiency anemia, megaloblastic anemia etc.) and hypertrophy low
Lower property anemia (such as aplastic anemia).
Clinically often from anemia pathogenesis and the classification of the cause of disease:
1. erythropoiesis minimizing property anemia
The anomalous effects erythropoiesis of hematopoietic cell, marrow stromal cell and hemopoietic raw material, can form erythrocyte raw
Become minimizing property anemia.
(1) hematopoietic stem/progenitor cells caused by abnormal anemia
1) aplastic anemia (AA) AA is a kind of marrow hematopoiesis function failure disease, with the primary and Hematopoietic Stem ancestral of secondary
Primary cellular defect is relevant.The pathogenesis of parts whole blood cytopenia and B cell produce anti-medullary cell autoantibody, and then broken
Go bad or suppression myeloid element is relevant.
2) pure red cell aplasia anemia (PRCA) PRCA refers to that bone marrow erythroid hematopoiesis stem/progenitor cells suffers damage, and then
Cause anemia.According to the cause of disease, this disease can be divided into congenital and posteriority two class.Congenital PRCA i.e. Diamond-Blackfan combines
Simulator sickness, is caused by heredity；Posteriority PRCA includes primary, secondary two class.Scholar is had to find part constitutional PRCA patients serum
In have self EPO or normoblast antibody.Secondary cases PRCA mainly have medicine relationship type, infect relationship type (antibacterial and virus, as
Piconavirus B19, hepatitis virus etc.), autoimmune disease relationship type, lymphoproliferative disease relationship type is (such as thymoma, pouring
Bar tumor, plasma cell dyscrasia and Lymphocytic leukemia etc.) and acute aplastic crisis etc..
3) congenital dyserythropoietic anemia (CDA) CDA is a class heritability red system optimum clone of stem/progenitor cells
Caused by abnormal, the refractory anemia that is characterized with red system ineffective hematopoiesis and paramophia.According to mode of inheritance, this disease can be divided into
Autosome hidden flight of steps leading to a palace hall genotype and dominant inheritance's type.
4) these disease hematopoietic stem/progenitor cells of hemopoietic system malignant clone disease there occurs the exception of matter, increases including bone marrow
Raw abnormal syndrome and all kinds of hematopoietic system cancer disease such as leukemia etc..The former is because DH, and high hypertrophy, height withers
Die, hemolysis in situ occurs；The latter's neoplastic hyperplasia, low apoptosis and low differentiation, hemopoietic regulation is also affected, so that normally becoming
Ripe erythrocytopenia and there is anemia.
(2) hematopoieticmicroenviron-ment caused by abnormal anemia
Hematopoieticmicroenviron-ment includes bone marrow matrix, stromal cell and cytokine.
1) bone marrow matrix and stromal cell impaired Anemia BMN, myelofibrosis, myelosclerosis, marble
The bone marrow neoplasms of extramedullary tumor diseases sick, various and various infection or non-infectious osteomyelitis, all can be because of damage bone marrow base
Matter and stromal cell, hematopoieticmicroenviron-ment occurs abnormal and affects hemopoietic.
2) hematopoietic regulators horizontal abnormality Anemia stem cell factor (SCF), interleukin (IL), grain-monosystem
Colony stimulating factor (GM-CSF), granulocyte-colony stimulating factor (G-CSF), erythropoietin (EPO), thrombopoietin
(TPO), PDGF (TGF), tumor necrosis factor (TNF) and interferon (IFN) etc. are respectively provided with positive negative regulation hemopoietic
Effect.EPO is produced not enough when renal insufficiency, hepatopathy and hypophysis or hypothyroidism etc.；Neoplastic disease or some disease
Poison infection can induce body to produce more hemopoietic negative regulatory factor such as TNF, IFN, inflammatory factor etc., all may result in chronic characteristic of disease
Anemia (ACD).
(3) hemopoietic insufficient raw material or Use barriers Anemia
Hemopoietic raw material refers to material necessary to hematopoietic cell proliferation, differentiation, metabolism, such as protein, lipid, vitamin
(folic acid, vitamin B12 etc.), trace element (ferrum, copper, zinc etc.) etc..Any one hemopoietic insufficient raw material or Use barriers all may
Erythropoiesis is caused to reduce.
1) folic acid or vitamin B12Lack or Use barriers Anemia causes body due to various physiology or pathological factor
The megaloblastic anemia that folic acid or vitamin B12 definitely or relatively lack or Use barriers can cause.
2) iron deficiency and ferrum Use barriers anemia this be the most modal anemia.Iron deficiency and ferrum Use barriers affect blood
Red pigment synthesizes, and having such anemia is called haemachrome resulting anomaly anemia.The red cell morphology of such anemia diminishes, central light dye
District expands, and belongs to microcytic hypochromic anemia.
2. hemolytic anemia (HA)
I.e. hematoclasis too much property anemia.
3. hemorrhagic anemia
Dividing acute and chronic according to speed of losing blood, chronic blood loss anemia often merges iron deficiency anemia.Can be divided into solidifying
Courageous and upright disease (such as idiopathic thrombocytopenic purpura, hemophilia and severe liver disease etc.) make peace non-go out disorders of blood coagulation (as
Wound, tumor, tuberculosis, bronchiectasis, peptic ulcer, hemorrhoid and gynaecopathia etc.) caused by two classes.
From natural product, find compound or lead compound and carry out structural modification and obtain its derivant, thus obtaining
The potential drug of high-efficiency low-toxicity most has important value.
The compound I that the present invention relates to be one within 2011, deliver (Fan-Yu Meng et al.,
2011.Schiglautone A,a New Tricyclic Triterpenoid with a Unique 6/7/9-Fused
Skeleton from the Stems of Schisandra glaucescens.Organic Letters 13(2011)
1502 1505) compound, we have carried out structural modification to compound I, it is thus achieved that two i.e. compounds of new derivant
III and compound IV, and it is prepared for compositions with compound III and compound IV and property low to said composition anti-erythrocyte is lean
Blood activity is evaluated, and it has anti-erythrocyte low property anemia activity.
Summary of the invention
The invention discloses a new compositions, said composition is made up of compound III and compound IV, said composition
The mass percent of middle compound III and compound IV is respectively 10% and 90%.
Compositions disclosed by the invention can make pharmaceutically acceptable salt or pharmaceutically acceptable carrier.
It is an object of the invention to provide the present composition new application in pharmaceutical field.
The present invention relates to compositions as the application in preparation treatment erythrocyte low property anemia medicine.
The present invention is further detailed explanation by the following examples, but protection scope of the present invention is not by concrete real
Execute any restriction of example, but be defined in the claims.
Detailed description of the invention
The preparation of embodiment 1 compound Schiglautone A
Document (the Fan-Yu that the preparation method of compound Schiglautone A (I) is delivered with reference to Fan-Yu Meng et al.
Meng et al.,2011.Schiglautone A,a New Tricyclic Triterpenoid with a Unique 6/
7/9-Fused Skeleton from the Stems of Schisandra glaucescens. Organic Letters
13 (2011) 1,502 1505) method.
The synthesis of O-bromoethyl derivant (II) of embodiment 2 Schiglautone A
Compound I (502mg, 1.00mmol) is dissolved in 15mL benzene, in solution, adds tetrabutyl ammonium bromide (TBAB)
(0.08g), glycol dibromide (7.520g, 40.00mmol) and 50% sodium hydroxide solution of 6mL.Mixture is Celsius 35
Degree stirring 8h.After 8h, reactant liquor is poured in frozen water, be extracted twice with dichloromethane immediately, merge organic phase solution.Then
Washing organic phase solution 3 times with water and saturated aqueous common salt successively, then be dried with anhydrous sodium sulfate, last concentrating under reduced pressure is removed molten
Agent obtains product crude product.Product crude product silica gel column chromatography purification (flowing is mutually: petroleum ether/acetone=100:1.0, v/v), receives
Collection brown is concentrated elution band and flings to solvent and i.e. obtain the brown ceramic powder (508mg, 71%) of compound II.
1H NMR(500MHz,DMSO-d6)δ13.40(s,1H),6.10(s,1H),5.63(s,1H),5.53(s,1H),
3.85 (d, J=11.2Hz, 4H), 3.52 (d, J=10.8Hz, 4H), 2.96 (s, 1H), 2.20 (s, 1H), 2.16 (s, 2H),
2.00 (s, 1H), 1.84 (d, J=13.9Hz, 4H), 1.69 (s, 1H), 1.58 (dd, J=22.2,8.5Hz, 4H), 1.51 (s,
1H), 1.47 (s, 1H), 1.26 (dd, J=9.1,4.4Hz, 4H), 1.21 (s, 1H), 1.08 0.98 (m, 4H), 0.96-0.94
(m,9H),0.94-0.85(m,6H).
13C NMR(125MHz,DMSO-d6)δ211.46(s),209.14(s),170.06(s),161.12(s),143.51
(s),132.01(s),127.77(s),85.96(s),82.40(s),70.19(s),69.10(s),57.14(s),52.73
(s),51.90(s),45.77(s),40.67(s),38.57(s),38.32(s),35.04(s),33.55(s),33.27(s),
29.85(s),28.98(s),26.71(s),25.50(s),24.05(s),22.31(s),21.06(s),20.56(s),20.00
(s),18.69(s),18.11(s),15.07(s).
HRMS(ESI)m/z[M-H]-calcd for C34H51Br2O6:715.2032；found 715.2027.
The synthesis of O-(the 1H-tetrazole base) ethyl derivative (III) of embodiment 3 Schiglautone A
Compound II (358mg, 0.5mmol) is dissolved in the middle of 15mL acetonitrile, be added thereto to Anhydrous potassium carbonate (345mg,
2.5mmol), potassium iodide (84mg, 0.5mmol) and 1H-tetrazole (1401mg, 20mmol), mixture is heated to reflux 5h.Reaction
Reactant liquor is poured in 20mL frozen water after end, extract three times with equivalent dichloromethane, merge organic facies.Successively with water and saturated
Organic facies after brine It merging, then be dried with anhydrous sodium sulfate, concentrating under reduced pressure is removed solvent and is obtained product crude product.Cause
For tautomerization, 1H-tetrazole base and two kinds of substitution products of 2H-tetrazole base can be generated at reaction conditions.Product is thick
Product silica gel column chromatography purification (flowing is mutually: petroleum ether/acetone=100:1, v/v), collects faint yellow concentration elution band, then will
Faint yellow elution band concentrates, and purifies (flowing is mutually: petroleum ether/acetone=100:0.5, v/v) with silica gel column chromatography, collects successively
Two flaxen elution bands, concentrate front 1 elution band and i.e. obtain the faint yellow solid (79.8mg, 23%) of compound III.
1H NMR(500MHz,DMSO-d6)δ16.29(s,1H),9.99(s,1H),9.93(s,1H),6.25(s,1H),
5.76 (s, 1H), 5.40 (s, 1H), 4.57 (s, 1H), 4.38 (s, 1H), 4.32 (s, 1H), 4.21 (s, 1H), 3.96 (d, J=
11.9Hz,4H),3.33(s,1H),2.55(s,1H),2.51(s,2H),2.39(s,1H),1.98(s,3H),1.82–1.76
(m, 3H), 1.73 (s, 1H), 1.65 (d, J=6.5Hz, 2H), 1.60 (s, 1H), 1.53 (s, 1H), 1.47 1.37 (m, 4H),
1.30 (s, 1H), 1.19 (s, 1H), 1.10 (t, J=12.5Hz, 3H), 1.08 (t, J=12.5Hz, 9H), 1.03 (s, 3H),
0.86(s,3H).
13C NMR(125MHz,DMSO-d6)δ211.72(s),209.42(s),170.36(s),161.38(s),145.37
(s),143.80(s),132.29(s),128.04(s),86.25(s),82.68(s),66.14(s),65.60(s),57.33
(s),52.91(s),52.08(s),46.81(s),45.95(s),40.84(s),38.76(s),38.50(s),35.21(s),
33.74(s),30.01(s),29.16(s),26.91(s),25.66(s),24.23(s),22.51(s),21.22(s),20.74
(s),20.20(s),18.85(s),18.29(s),15.27(s).
HRMS(ESI):m/z[M+H]+calcd for C36H55N8O6:695.4245；found:695.4248.
The synthesis of O-(benzimidazolyl) ethyl derivative of embodiment 4Schiglautone A
Compound II (358mg, 0.5mmol) is dissolved in the middle of 15mL acetonitrile, be added thereto to Anhydrous potassium carbonate (345mg,
2.5mmol), potassium iodide (84mg, 0.5mmol) and benzimidazole (1180mg, 10mmol), mixture is heated to reflux 6h.Reaction
After end, reactant liquor is poured in frozen water, extract three times with equivalent dichloromethane, merge organic facies.Successively with water and saturated common salt
Organic facies after water washing merging, then be dried with anhydrous sodium sulfate, concentrating under reduced pressure is removed solvent and is obtained product crude product.Product is thick
Product silica gel column chromatography purification (flowing is mutually: petroleum ether/acetone=100:1.5, v/v), collects brown and concentrates elution band, concentrate
I.e. obtain the brown solid (169.9mg, 43%) of compound IV.
1H NMR (500MHz, DMSO-d6) δ 13.32 (s, 1H), 8.38 (s, 2H), 7.66 (d, J=25.0Hz, 4H),
(7.39 s, 2H), 7.32 (s, 2H), 6.25 (s, 1H), 5.64 (d, J=18.7Hz, 2H), 4.34 (s, 1H), 4.28 (s, 1H),
4.18 (d, J=13.7Hz, 2H), 4.04 (s, 2H), 3.99 (s, 2H), 3.13 (s, 1H), 2.65 (s, 2H), 2.26 (s, 1H),
2.17 (s, 1H), 2.06 (s, 1H), 1.98 (s, 3H), 1.87 (d, J=16.4Hz, 2H), 1.66 (dd, J=8.0,6.6Hz,
4H), 1.62 (s, 1H), 1.49 (s, 1H), 1.41 (dd, J=19.6,10.4Hz, 2H), 1.37 (d, 2H), 1.20 1.11 (m,
4H), 1.07 (d, J=20.0Hz, 6H), 103 (d, J=20.0Hz, 3H), 1.01 (d, J=20.0Hz, 3H), 0.95 (d, J=
20.0Hz,3H).
13C NMR(125MHz,DMSO-d6)δ211.30(s),208.98(s),169.90(s),160.96(s),146.28
(s),143.34(s),139.64(s),133.48(s),131.85(s),127.61(s),123.92(s),123.35(s),
118.55(s),110.85(s),85.79(s),82.26(s),67.74(s),67.20(s),57.00(s),52.56(s),
51.73(s),45.63(s),44.94(s),40.49(s),38.42(s),38.17(s),34.86(s),33.40(s),29.68
(s),28.81(s),26.57(s),25.33(s),23.88(s),22.17(s),20.89(s),20.39(s),19.86(s),
18.52(s),17.87(s),14.93(s).
HRMS(ESI):m/z[M+H]+calcd for C48H63N4O6:791.4748；found:791.4744.
Embodiment 5 compositions anti-erythrocyte low property anemia is tested
Test 1 compositions therapeutical effect to post hemorrhagic mice
ICR mice 30, ♀ ♂ half and half, it is divided into 5 groups (n=10).In addition to normal saline group, other every mice of group from
Orbital vein blood-letting 0.5ml, takes blood again and surveys and all respectively organize index after 24h, then every day after gastric infusion 1 week and administration continuously
Blood-letting 0.5ml, after last is administered 1h, takes the full whole bliid platelet analyzer of blood F-800 from orbital venous plexus and carries out red blood cell count(RBC)
(1012/L)。
The preparation of compositions: the powder that will cross the 10mg compound III of 200 mesh nets after grinding crosses 200 after grinding
The powder of the 90mg compound IV of mesh net loads in tubule with cover and i.e. obtains 100mg compositions with the mixing of turbine stirring instrument,
Obtain the solution of compositions by the compositions of this 100mg of water dissolution during use.
Table 1 compositions is to because of caused oligocythemic therapeutical effect of losing blood
Compare with model group: * p < 0.05
Result shows, blood-letting mice, after taking compositions and treating 7 days, is compared with model group, and its erythrocyte is significantly higher than
Model group, close to normal saline group.And compound III and compound IV acts on without this.
Two, compositions causes oligocythemic therapeutical effect to cyclophosphamide
Preventive and therapeutic effect ICR mice 50 to the damage of mouse bone marrow cells hemopoietic function, ♀ ♂ dual-purpose, it is divided into 5 groups (n=10),
I.e. normal saline group, modeling group, compositions 1.2mg/kg group, compound III 1.2mg/kg group and compound IV 1.2mg/kg
Group, oral administration, every day 1 time.In addition to normal saline group, other respectively organized mice lumbar injection cycli phosphate amine respectively on 0th, 5,10th
80mg/kg, then proceedes to be administered 3 days.1h after last is administered, takes blood from orbital venous plexus, surveys RBC number (1012/L)。
The impact erythrocytic on caused by cyclophosphamide of table 2 compositions
Compare with model group: * * p < 0.01
Result shows, compares with normal saline group, and cycli phosphate amine can make mouse bone marrow cells damage, and causes under peripheral blood cells
Fall, compositions group compares with model group, can substantially resist cycli phosphate amine induced mice red blood cell decreased.And compound III and change
Compound IV acts on without this.
Three, compositions is to therapeutical effect oligocythemic caused by benzene
Impact on Induced Aplastic Anemia Mice: Kunming mouse 50, ♀ ♂ dual-purpose, it is divided into 5 groups (n=10), removes
Outside normal saline group, other organizes mouse subcutaneous injection benzene 0.5ml/kg, continuous 12 days, the same day of modeling, simultaneously oral administration, often
It 1 time, totally 18 days, 1h after last administration, orbital venous plexus took blood, surveys erythrocyte.
Table 3 compositions is to therapeutical effect oligocythemic caused by benzene
Compare with model group: * * p < 0.01
Result shows, compositions group compares with model group, can substantially resist Induced Aplastic Anemia Mice caused by benzene red carefully
The decline of born of the same parents.And compound III and compound IV acts on without this.
Conclusion: compositions can significantly raise erythrocyte, can be used to the medicine of preparation treatment anemia.And compound III
Erythrocyte can not be significantly raised, it is impossible to be used for preparing the medicine for the treatment of anemia with compound IV.
The preparation of embodiment 6 composition tablet involved in the present invention
Taking 2 grams of compositionss, the customary adjuvant 18 grams of tablet is prepared in addition, and mixing, conventional tablet presses makes 100.
The preparation of embodiment 7 composition capsule involved in the present invention
Taking 2 grams of compositionss, the customary adjuvant such as starch 18 grams of capsule is prepared in addition, mixing, encapsulated makes 100.
Claims (7)
1. a compositions, is characterized by that said composition is made up of compound III and compound IV, compound in said composition
The mass percent of III and compound IV is respectively 10% and 90%,
2. the preparation method of compositions as claimed in claim 1, is characterized by: by powder and the compound IV of compound III
Powder be sufficiently mixed according to mass percent respectively 10% and 90%.
3. a compositions as claimed in claim 1 application in treatment erythrocyte low property anemia medicine.
4. the compositions as claimed in claim 3 application in treatment erythrocyte low property anemia medicine, is characterized by: described
Erythrocyte low property anemia is caused by losing blood.
5. the compositions as claimed in claim 3 application in treatment erythrocyte low property anemia medicine, is characterized by: described
Erythrocyte low property anemia is low by the erythrocyte caused by chemical substance.
6. the compositions as claimed in claim 5 application in treatment erythrocyte low property anemia medicine, is characterized by: described
Chemical substance is benzene, and described erythrocyte low property anemia is by the aplastic anemia caused by benzene.
7. the compositions as claimed in claim 5 application in treatment erythrocyte low property anemia medicine, is characterized by: described
Chemical substance is cycli phosphate amine, and described erythrocyte low property anemia is by red blood cell decreased caused by cycli phosphate amine.
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Cited By (1)
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| CN106539784A (en) * | 2016-11-04 | 2017-03-29 | 徐州诺克非医药科技有限公司 | The purposes of the pharmaceutical composition containing Schiglautone A and its raising Lactoferrin content |
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| CN104800222A (en) * | 2015-04-29 | 2015-07-29 | 南京大学 | Application of O-(benzimidazolyl) ethyl derivative of cleistanone in preparing drug for preventing red blood cell hypoplastic anemia |
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Application publication date: 20161026 |