CN115557952A - Penta-seven-membered aza-condensed ring compound and preparation method thereof - Google Patents
Penta-seven-membered aza-condensed ring compound and preparation method thereof Download PDFInfo
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- CN115557952A CN115557952A CN202211252899.7A CN202211252899A CN115557952A CN 115557952 A CN115557952 A CN 115557952A CN 202211252899 A CN202211252899 A CN 202211252899A CN 115557952 A CN115557952 A CN 115557952A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 39
- 238000002360 preparation method Methods 0.000 title description 5
- 238000006243 chemical reaction Methods 0.000 claims abstract description 24
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 84
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 28
- 229910052757 nitrogen Inorganic materials 0.000 claims description 23
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 14
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 14
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 125000003277 amino group Chemical group 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 239000011541 reaction mixture Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 150000001721 carbon Chemical group 0.000 claims 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 19
- 238000011160 research Methods 0.000 abstract description 6
- 230000000694 effects Effects 0.000 abstract description 4
- 229940125904 compound 1 Drugs 0.000 description 14
- 230000015572 biosynthetic process Effects 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- 238000003756 stirring Methods 0.000 description 9
- 238000010792 warming Methods 0.000 description 9
- 230000035945 sensitivity Effects 0.000 description 7
- MLOXIXGLIZLPDP-UHFFFAOYSA-N 2-amino-1h-imidazole-4,5-dicarbonitrile Chemical compound NC1=NC(C#N)=C(C#N)N1 MLOXIXGLIZLPDP-UHFFFAOYSA-N 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
- 238000011161 development Methods 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 229940125782 compound 2 Drugs 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 2
- 229940125898 compound 5 Drugs 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000007306 functionalization reaction Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000005580 one pot reaction Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- NDGSDCLCVGQSKB-UHFFFAOYSA-N 1h-pyrazole-4,5-dicarbonitrile Chemical compound N#CC1=CNN=C1C#N NDGSDCLCVGQSKB-UHFFFAOYSA-N 0.000 description 1
- RHEFLWRCYOAOTQ-UHFFFAOYSA-N 2-nitro-1h-imidazole-4,5-dicarbonitrile Chemical compound [O-][N+](=O)C1=NC(C#N)=C(C#N)N1 RHEFLWRCYOAOTQ-UHFFFAOYSA-N 0.000 description 1
- IVANFNGOSJTZFM-UHFFFAOYSA-N 2h-triazole-4,5-dicarbonitrile Chemical compound N#CC1=NNN=C1C#N IVANFNGOSJTZFM-UHFFFAOYSA-N 0.000 description 1
- -1 3-Nitro-4, 5-dicyanopyrazole Chemical compound 0.000 description 1
- ZPICOUKAFAPIOK-UHFFFAOYSA-N 3-amino-1h-pyrazole-4,5-dicarbonitrile Chemical compound NC1=NNC(C#N)=C1C#N ZPICOUKAFAPIOK-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000002411 thermogravimetry Methods 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C06—EXPLOSIVES; MATCHES
- C06B—EXPLOSIVES OR THERMIC COMPOSITIONS; MANUFACTURE THEREOF; USE OF SINGLE SUBSTANCES AS EXPLOSIVES
- C06B25/00—Compositions containing a nitrated organic compound
- C06B25/34—Compositions containing a nitrated organic compound the compound being a nitrated acyclic, alicyclic or heterocyclic amine
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
The invention discloses a five-and seven-membered aza fused ring compound, which enriches the variety of aza fused ring skeletons by a fused ring compound formed by five-membered aza heterocyclic and seven-membered aza rings, widens the reaction activity of the compound by introducing amino, lays a foundation for the research of novel energetic materials based on the aza fused ring skeletons, and provides a new idea.
Description
Technical Field
The invention relates to the technical field of energetic materials, in particular to a penta-hepta-aza fused ring compound and a preparation method thereof.
Background
The energetic material is an energy source material which is related to the national strategic safety and is an energy source for propelling, launching and damaging a weapon system. With the continuous change of international forms and the development of times, the requirements on energetic materials are higher and higher, especially the safety performance to cope with unstable factors in the manufacturing, transportation, use and storage processes.
The aza-condensed ring framework is a framework formed by combining two or more aza rings, and is widely applied to low-sensitivity high-energy materials, and a novel energy-containing material based on the aza-condensed ring framework becomes a current research hotspot. However, at present, the skeleton of the aza-condensed ring is mainly limited to five-membered ring and five-membered ring, five-membered ring and six-membered ring, and the like, the number of the skeleton of the aza-condensed ring is small, and because the skeleton needs to be modified by high-energy groups, the modified sites of the skeleton are usually few, and the development of the novel low-sensitivity high-energy-content material is limited to a certain extent. Therefore, in view of the current situation that the number of types of aza-condensed ring skeletons is small, the development of a novel aza-condensed ring skeleton is very important in the field of novel energetic materials.
Disclosure of Invention
An object of the present invention is to solve at least the above problems and/or disadvantages and to provide at least the advantages described hereinafter.
The invention also aims to provide a five-membered and seven-membered aza fused ring compound, which enriches the variety of aza fused ring frameworks by the fused ring compound formed by five-membered aza ring and seven-membered aza rings, widens the reaction activity of the compound by introducing amino, lays a foundation for the research of novel energetic materials based on the aza fused ring frameworks, and provides a new idea.
Still another object of the present invention is to provide a method for preparing a penta-seven membered aza-fused ring compound, which successfully synthesizes the penta-seven membered aza-fused ring compound through one-step reaction from the known available raw materials, enriches the variety of aza-fused ring skeletons, lays a foundation for the research of novel energetic materials based on aza-fused ring skeletons, and provides a new idea.
To achieve these objects and other advantages in accordance with the present invention, there is provided a penta-seven membered azacondensed ring compound, wherein the energy-containing compound has the following structure of formula (I):
wherein X and Y are independently carbon atom or nitrogen atom, R 1 、R 2 、R 3 、R 4 、R 5 Independently hydrogen, nitro or amino.
Preferably, X and Y are independently carbon atom or nitrogen atom, R 1 Is nitro or amino, R 2 Is hydrogen, nitro or amino, R 3 、R 4 、R 5 Are all amino groups.
Preferably, wherein X is a carbon atom, Y is a nitrogen atom, R 1 Is nitro or amino, R 3 、R 4 、R 5 Are all amino groups.
Preferably, wherein X is a nitrogen atom, Y is a carbon atom, R 2 Is hydrogen, nitro or amino, R 3 、R 4 、R 5 Are all amino groups.
Preferably, wherein X is a carbon atom, Y is a nitrogen atom, R 1 Is amino, R 3 、R 4 、R 5 Are all amino groups.
Preferably, wherein X is a nitrogen atom, Y is a nitrogen atom, R 3 、R 4 、R 5 Are all amino groups.
The object of the present invention can be further achieved by a process for producing a penta-and hepta-membered aza fused ring compound, comprising the steps of: adding dicyano-substituted five-membered azacyclo into a solvent, adding guanidine into a reaction mixture for reaction, filtering and recrystallizing after the reaction is finished to obtain a target compound, namely a compound shown as a formula (I) ；
Wherein, the dicyano-substituted five-membered nitrogen heterocycle has the following structure as shown in the formula (II):
preferably, the molar ratio of the dicyano-substituted five-membered nitrogen heterocycle to the guanidine is 1: 1.0-1: 1.5.
Preferably, the reaction temperature is 60-85 ℃ and the reaction time is 10-48 h.
Preferably, the solvent is one of methanol, ethanol, acetone and acetonitrile.
The invention at least comprises the following beneficial effects:
1. the five-membered nitrogen heterocyclic and seven-membered nitrogen heterocyclic form the fused ring compound, and the five-membered and seven-membered fused ring skeleton has better aromaticity than five-membered and five-membered fused rings and five-membered and six-membered fused rings, and is favorable for obtaining better stability and safety performance. Because the seven-membered ring has more modified sites than the six-membered ring, a richer novel energetic material can be obtained through functionalization. The invention enriches the variety of aza-condensed ring skeletons, widens the reaction activity of the compound by introducing amino, lays a foundation for the research of novel energetic materials based on the aza-condensed ring skeletons, and provides a new idea.
2. The preparation method of the penta-hepta-aza fused ring compound provided by the invention starts from known raw materials, and successfully synthesizes azole energetic compounds through one-step reaction. The synthesized azole energetic compound has the potential of being used as an energetic material.
Additional advantages, objects, and features of the invention will be set forth in part in the description which follows and in part will become apparent to those having ordinary skill in the art upon examination of the following or may be learned from practice of the invention.
Drawings
FIG. 1 is a DSC of Compound 1 of example 1 of the present invention;
FIG. 2 is a nuclear magnetic resonance hydrogen spectrum of Compound 1 in example 1 of the present invention;
FIG. 3 is a NMR spectrum of Compound 1 in example 1 of the present invention.
Detailed Description
The present invention is further described in detail below with reference to the attached drawings so that those skilled in the art can implement the invention by referring to the description text.
It will be understood that terms such as "having," "including," and "comprising," as used herein, do not preclude the presence or addition of one or more other elements or groups thereof.
It is to be noted that the experimental methods described in the following embodiments are all conventional methods unless otherwise specified, and the reagents and materials are commercially available unless otherwise specified.
< example 1>
A penta-hepta-azacondensed ring compound 1 having the structural formula:
the specific synthetic route is as follows:
the specific synthesis steps are as follows:
2-amino-4, 5-dicyanoimidazole (133.0 mg,1.0 mmol) was dissolved in 15mL of ethanol, a solution of guanidine (64.9 mg,1.1 mmol) in methanol was added thereto at room temperature, followed by warming to 80 ℃ and stirring for reaction for 10 hours. The reaction mixture was then cooled to room temperature, filtered, and recrystallized from methanol to obtain the objective compound 1 (117.1 mg, yield 61%). The NMR spectrum of compound 1 is shown in FIG. 2, and the NMR spectrum is shown in FIG. 3.
< example 2>
The difference from the example 1 is:
the specific synthesis steps are as follows:
2-amino-4, 5-dicyanoimidazole (133.0 mg,1.0 mmol) was dissolved in 15mL of methanol, a methanol solution of guanidine (88.5 mg,1.5 mmol) was added thereto at room temperature, followed by warming to 70 ℃ and stirring for reaction for 24 hours. The reaction mixture was then cooled to room temperature, filtered, and recrystallized from methanol to obtain the objective compound 1 (140.2 mg, 73% yield).
< example 3>
The difference from the example 1 is:
the specific synthesis steps are as follows:
2-amino-4, 5-dicyanoimidazole (133.0 mg,1.0 mmol) was dissolved in 15mL of methanol, a solution of guanidine (70.8mg, 1.2mmol) in methanol was added thereto at room temperature, and the reaction was stirred at room temperature to 70 ℃ for 36 hours. The reaction mixture was then cooled to room temperature, filtered, and recrystallized from methanol to obtain the objective compound 1 (155.5 mg, yield 81%).
< example 4>
The difference from the example 1 is:
the specific synthesis steps are as follows:
2-amino-4, 5-dicyanoimidazole (133.0 mg,1.0 mmol) was dissolved in 15mL of acetonitrile, and a solution of guanidine (76.7 mg,1.3 mmol) in methanol was added thereto at room temperature, followed by warming to 85 ℃ and stirring for reaction for 36 hours. The reaction was then cooled to room temperature, filtered, and recrystallized from methanol to give the objective compound 1 (149.8 mg, 78% yield).
< example 6>
The difference from the example 1 is:
the specific synthesis steps are as follows:
2-amino-4, 5-dicyanoimidazole (133.0 mg,1.0 mmol) was dissolved in 15mL of acetone, a solution of guanidine (59.0 mg,1.0 mmol) in methanol was added thereto at room temperature, followed by warming to 60 ℃ and stirring for reaction for 48 hours. The reaction mixture was then cooled to room temperature, filtered, and recrystallized from methanol to obtain the objective compound 1 (115.2 mg, yield 60%).
< example 7>
A penta-heptamembered azacondensed ring compound 2 having the formula:
the specific synthetic route is as follows:
the specific synthesis steps are as follows:
4, 5-dicyano-1H-1, 2, 3-triazole (119mg, mmol) was dissolved in 10mL of acetonitrile, and a solution of guanidine (70.8mg, 1.2mmol) in methanol was added thereto at room temperature, followed by warming to 100 ℃ and stirring for reaction for 10 hours. The reaction was then cooled to room temperature, filtered, and recrystallized from methanol to give the objective compound 2 (115.7 mg, 65% yield).
< example 8>
A penta-hepta azacondensed ring compound 3 having the following structural formula:
the specific synthetic route is as follows:
the specific synthesis steps are as follows:
2-Nitro-4, 5-dicyanoimidazole (163mg, 1mmol) was dissolved in 15mL of methanol, and a solution of guanidine (70.8mg, 1.2mmol) in methanol was added thereto at room temperature, followed by warming to 76 ℃ and stirring for reaction for 36 hours. The reaction mixture was then cooled to room temperature, filtered, and recrystallized from methanol to obtain the objective compound 3 (179.8 mg, yield 81%).
< example 9>
A penta-heptamembered azacondensed ring compound 4 having the formula:
the specific synthetic route is as follows:
the specific synthesis steps are as follows:
4, 5-dicyanopyrazole (118mg, 1mmol) was dissolved in 10mL of methanol, to which a solution of guanidine (70.8mg, 1.2mmol) in methanol was added at room temperature, followed by warming to 78 ℃ and stirring for reaction for 36h. The reaction was then cooled to room temperature, filtered, and recrystallized from methanol to give the title compound 4 (138 mg, 78% yield).
< example 10>
A penta-heptamembered azacondensed ring compound 5 having the formula:
the specific synthetic route is as follows:
the specific synthesis steps are as follows:
3-amino-4, 5-dicyanopyrazole (133mg, 1mmol) was dissolved in 15mL of methanol, and a solution of guanidine (70.8mg, 1.2mmol) in methanol was added thereto at room temperature, followed by warming to 75 ℃ and stirring for reaction for 48 hours. The reaction was then cooled to room temperature, filtered, and recrystallized from methanol to give the objective compound 5 (138.2 mg, yield 72%).
< example 11>
A penta-heptamembered azacondensed ring compound 6 having the formula:
the specific synthetic route is as follows:
the specific synthesis steps are as follows:
3-Nitro-4, 5-dicyanopyrazole (163mg, 1mmol) was dissolved in 15mL of methanol, and a solution of guanidine (70.8mg, 1.2mmol) in methanol was added thereto at room temperature, followed by warming to 60 ℃ and stirring for reaction for 48 hours. The reaction mixture was then cooled to room temperature, filtered, and recrystallized from methanol to obtain the objective compound 6 (146.5 mg, yield 66%).
< example 12>
DSC thermogravimetric analysis property test experiment is carried out on the penta-hepta aza-condensed ring compound 1 synthesized in the embodiment 1 of the invention:
compound 1 (1.0 ± 0.1 mg) was tested, conditions tested: the temperature of a standard aluminum crucible is 25-400 ℃, the heating rate is 10 ℃/min, and the nitrogen flow is 50mL/min. The results of the tests are shown in fig. 1, from which it can be concluded that compound 1 shows a decomposition temperature of 344 ℃ and is obtained by the sensitivity performance test: the impact sensitivity is more than 40J, the friction sensitivity is more than 360N, and the compound has excellent thermal stability and safety performance.
The impact sensitivity and the friction sensitivity are key factors for expressing the safety of the energetic compound, and the higher and the more insensitive the numerical value, the more insensitive the stability of the insensitive energetic material is, and the safer the use and the storage are.
The condensed ring compound formed by five-membered nitrogen heterocycle and seven-membered nitrogen heterocycle enriches the variety of nitrogen-condensed ring frameworks, widens the reaction activity of the compound by introducing amino, lays a foundation for the research of novel energetic materials based on the nitrogen-condensed ring frameworks, and provides a new idea. The existing aza-condensed ring skeleton mainly comprises five-membered ring and five-membered ring, five-membered ring and six-membered ring, and the development of novel low-sensitivity high-energy energetic materials is limited to a certain extent. The seven-membered ring has more modification sites than the six-membered ring, and a richer novel energetic material can be obtained through functionalization. The invention provides a brand-new 5/7 aza-condensed ring framework of five-membered ring and seven-membered ring and a preparation method thereof, the framework has higher aromaticity than 5/5 condensed rings and 5/6 condensed rings, and better stability and safety performance can be obtained. If the decomposition peak temperature of the compound 1 reaches 344 ℃, the friction sensitivity test limit value is more than 360N, the impact sensitivity is more than 40J, and the thermal stability and the safety performance are excellent.
While embodiments of the invention have been disclosed above, it is not intended to be limited to the uses set forth in the specification and examples. It can be applied to all kinds of fields suitable for the present invention. Additional modifications will readily occur to those skilled in the art. It is therefore intended that the invention not be limited to the exact details and illustrations described and illustrated herein, but fall within the scope of the appended claims and equivalents thereof.
Claims (10)
1. A penta-heptamembered aza fused ring compound, the energetic compound having the structure of formula (I):
wherein X and Y are independently carbon atom or nitrogen atom, R 1 、R 2 、R 3 、R 4 、R 5 Independently hydrogen, nitro or amino.
2. The penta-seven membered aza fused ring compound of claim 1 wherein X, Y are independently carbon or nitrogen, R 1 Is nitro or amino, R 2 Is hydrogen, nitro or amino, R 3 、R 4 、R 5 Are all amino groups.
3. The penta-seven membered aza fused ring compound as claimed in claim 1, wherein X is carbon atom, Y is nitrogen atom, R is 1 Is nitro or amino, R 3 、R 4 、R 5 Are all amino groups.
4. The penta-seven membered aza fused ring compound according to claim 1, wherein X is a nitrogen atom, Y is a carbon atom, R 2 Is hydrogen, nitro or amino, R 3 、R 4 、R 5 Are all amino groups.
5. The penta-seven membered aza fused ring compound as claimed in claim 1, wherein X is carbon atom, Y is nitrogen atom, R is 1 Is amino, R 3 、R 4 、R 5 Are all amino groups.
6. The penta-seven membered aza fused ring compound of claim 1 wherein X is nitrogen atom, Y is nitrogen atom, R 3 、R 4 、R 5 Are all amino groups.
7. A process for preparing a penta-and hepta-azacondensed ring compound according to any one of claims 1 to 6, comprising the steps of:
adding dicyano-substituted five-membered azacycle into a solvent, then adding guanidine into a reaction mixture for reaction, and after the reaction is finished, filtering and recrystallizing to obtain a target compound, namely a compound shown in formula (I);
wherein, the dicyano substituted five-membered nitrogen heterocycle has the following structure of formula (II):
8. the method of claim 7, wherein the molar ratio of dicyano-substituted five-membered nitrogen heterocycle to guanidine is 1: 1.0 to 1: 1.5.
9. The process of claim 7, wherein the reaction temperature is 60-85 ℃ and the reaction time is 10-48 h.
10. The method of claim 7, wherein the solvent is one of methanol, ethanol, acetone, and acetonitrile.
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Non-Patent Citations (2)
| Title |
|---|
| RAHILA MATTOHTI: "A study of the aromaticity and ring currents of azulene and azaazulenes", 《RSC ADV.》, vol. 6, pages 1 * |
| XIE, MIN: "Synthesis, anticancer activity, and SAR analyses of compounds containing the 5:7-fused 4, 6, 8-triaminoimidazo[4, 5-e][1, 3]diazepine ring system", 《BIOORGANIC & MEDICINAL CHEMISTRY》, vol. 24, no. 12, pages 2597 * |
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