N-(46-二氯-5-硝基嘧啶-2-基)乙酰胺 | 56145-04-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: N-(46-二氯-5-硝基嘧啶-2-基)乙酰胺
• 中文别名: N-(4,6-二氯-5-硝基嘧啶-2-基)乙酰胺
• 英文名称: N1-(4,6-Dichloro-5-nitro-2-pyrimidinyl)acetamide
• 英文别名: N-(4,6-dichloro-5-nitropyrimidin-2-yl)acetamide；2-acetamido-4,6-dichloro-5-nitro-pyrimidine；2-acetamino-4,6-dichloro-5-nitropyrimidine；N-acetyl-4,6-dichloro-5-nitropyrimidine；N-(4,6-dichloro-5-nitro-pyrimidin-2-yl)-acetamide
• CAS: 56145-04-1
• 化学式: C₆H₄Cl₂N₄O₃
• 分子量: 251.029
• InChiKey: JTLCZWOWLVTEOB-UHFFFAOYSA-N

物化性质

• 熔点：
  224 °C
• 密度：
  1.734±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2933599090

反应信息

• 作为反应物：
  描述：

  N-(46-二氯-5-硝基嘧啶-2-基)乙酰胺 在 镍 氢气 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 4.0~20.0 ℃ 、101.33 kPa 条件下， 反应 9.0h， 生成
  参考文献：
  名称：

  2-Alkynyl-8-aryl-9-methyladenines as Novel Adenosine Receptor Antagonists:  Their Synthesis and Structure−Activity Relationships toward Hepatic Glucose Production Induced via Agonism of the A_2B Receptor

  摘要：

  Novel adenosine antagonists, 2-alkynyl-8-aryl-9-methyladenine derivatives, were synthesized as candidate hypoglycemic agents. These analogues were evaluated for inhibitory activity on N-ethylcarboxamidoadenosine (NECA)-induced glucose production in primary cultured rat hepatocytes. In general, aromatic moieties at the 8-position and alkynyl groups at the 8-position had significantly increased activity compared to unsubstituted compounds. The preferred substituents at the 8-position of adenine were the 2-furyl and 3-fluorophenyl groups. In modifying the alkynyl side chain, change of the ring size, cleavage of the ring, and removal of the hydroxyl group were well tolerated. The order of the stimulatory effects of adenosine agonists on rat hepatocytes was NECA > CPA > CGS21680, which is consistent with involvement of the A(2B) receptor. In Chinese hamster ovary cells stably transfected with human A(2B) receptor cDNA, one of the compounds potent in hepatocytes, 15o (IC50 = 0.42 muM), antagonized NECA-induced stimulation of cyclic AMP production (IC50 = 0.063 muM). This inhibitory effect was much more potent than those of FK453, KF17837, and L249313 which have been reported to be respectively A(1), A(2A), and A(3) selective antagonists. These findings agree very well with the result that, compared to 15o, these selective antagonists for each receptor subtype showed only marginal effects in rat hepatocytes. These results suggest that adenosine agonist-induced glucose production in rat hepatocytes is mediated through the A(2B) receptor. Furthermore, 15o showed hypoglycemic activity in an animal model of noninsulin-dependent diabetes mellitus, the KK-A(y) mice. It is possible that inhibition of hepatic glucose production via the A(2B) receptor could be at least one of the mechanisms by which 15o exerts its in, vivo effects. Further elaboration of this group of compounds may afford novel antidiabetic agents.

  DOI：

  10.1021/jm990499b
• 作为产物：
  描述：

  N-(6-氯-5-硝基-4-氧代-1,4-二氢嘧啶-2-基)乙酰胺 、 三氯氧磷 以67%的产率得到
  参考文献：
  名称：

  TEMPLE JR. C.; SMITH B. H.; MONTGOMERY J. A., J. ORG. CHEM. , 1975, 40, NO 21, 3141-3142

  摘要：

  DOI：

文献信息

• Synthesis of neplanocin F analogues as potential antiviral agents
  作者：Hongwang Zhang、Raymond F. Schinazi、Chung K. Chu

  DOI：10.1016/j.bmc.2006.09.007

  日期：2006.12

  Neplanocin F is a natural carbocyclic nucleoside. Herein, we describe the synthesis and antiviral activity of (+/-)-5'-deoxy-neplanocin F analogues. The key intermediate 4, synthesized from the commercially available (+/-)-2-azabicyclo[2.2.1]-hept-5-en-3-one (ABH), was utilized to prepare the target nucleosides. Among the target compounds, 5'-deoxyneplanocin F adenine exhibited moderate anti-HIV activity

  Neplanocin F是天然的碳环核苷。在本文中，我们描述了（+/-）-5'-脱氧-neplanocin F类似物的合成和抗病毒活性。由市售的（+/-）-2-氮杂双环[2.2.1]-庚-5-烯-3-酮（ABH）合成的关键中间体4，用于制备目标核苷。在目标化合物中，5'-脱氧内啡肽F腺嘌呤在人淋巴细胞中表现出中等的抗HIV活性，而没有任何明显的细胞毒性。
• Spiropentane Mimics of Nucleosides:  Analogues of 2‘-Deoxyadenosine and 2‘-Deoxyguanosine. Synthesis of All Stereoisomers, Isomeric Assignment, and Biological Activity
  作者：Hui-Ping Guan、Mohamad B. Ksebati、Yung-Chi Cheng、John C. Drach、Earl R. Kern、Jiri Zemlicka

  DOI：10.1021/jo991030r

  日期：2000.3.1

  introduced into individual isomers 25a-25d via 6-chloropurine derivatives 26a-26d or 30a-30d. Ammonolysis of 26a-26d furnished the adenine isomeric series 12a-15a, whereas guanine derivatives 12b-15b were obtained by hydrolysis of 30a-30d with formic acid. The isomeric assignments followed from IR spectra of BOC-aminospiropentanes 24a-24d and NMR spectra of 12a-15a including NOE and (H,H) COSY. The proximal

  描述了2'-脱氧腺苷和2'-脱氧鸟苷（12a-15a和12b-15b）的螺环类似物的合成。铑经重溴化反应（16），还原反应（18）和乙酰化反应（19）从2-溴-2-溴甲基环丙烷17制得的重氮乙酸乙酯与亚甲基环丙烷19的催化反应，得到了所有四种异构的螺环戊烷20a-20d的混合物。水解得到羟基羧酸21a-21d。分离的近端+内侧-syn异构体21a + 21b和内侧抗+远端+异构体21c + 21d的乙酰化提供了乙酸酯22a + 22b和22c + 22d。由二苯基磷酰基叠氮化物在叔丁醇中分别与混合物22a + 22b和22c + 22d进行的Curtius重排导致BOC-氨基螺环戊烷23a + 23b和23c + 23d。脱乙酰基后，分离所有异构体24a-24d并脱保护，得到氨基螺戊烷盐酸盐25a-25d。游离碱的稳定性有限。经由6-氯嘌呤衍生物26a-26d或30a-30d将杂环部分引入
• Synthesis of (±)-cycloprop-G, the cyclopropyl analogue of the broad spectrum antiviral agent cyclobut-G
  作者：Daniel W. Norbeck、Hing L. Sham、Thomas Herrin、William Rosenbrook、Jacob J. Plattner

  DOI：10.1039/c39920000128

  日期：——

  An efficient synthesis of (±)-cycloprop-G from Feist's acid is described.

  介绍了从费斯特酸中高效合成 (±)- 环丙-G。
• Purine derivatives and adenosine A2 receptor antagonists serving as preventives/remedies for diabetes
  申请人：Eisai Co., Ltd.

  公开号：US06579868B1

  公开（公告）日：2003-06-17

  The present invention provides a preventive or therapeutic agent of a new type for diabetes mellitus and diabetic complications on the basis of an adenosine A2 receptor antagonistic action. A purine compound represented by the formula (I), its pharmacologically acceptable salt or hydrates thereof has an adenosine A2 receptor antagonistic action and is useful for prevention or therapy of diabetes mellitus and diabetic complications. In addition, adenosine A2 receptor antagonists having different structures from those of the compounds described above, for example KW6002, are also effective for prevention or therapy of diabetes mellitus and diabetic complications. In the formula, W is —CH2CH2—, —CH═CH— or —C≡C—; R1 is: (in the formula, X is hydrogen atom, hydroxyl group, a lower alkyl group, a lower alkoxy group, etc.; and R5 and R6 are the same as or different from each other and each represents hydrogen atom, a lower alkyl group, a cycloalkyl group, etc.) and the like; R2 is an amino group, etc. which maybe substituted with a lower alkyl group, etc.; R3 is a cycloalkyl group, an optionally substituted aryl group, etc.; and R4 is a lower alkyl group etc.

  本发明提供了一种基于腺苷A2受体拮抗作用的新型糖尿病和糖尿病并发症的预防或治疗剂。公式（I）所代表的嘌呤化合物及其药学上可接受的盐或水合物具有腺苷A2受体拮抗作用，并且对于糖尿病和糖尿病并发症的预防或治疗非常有用。此外，与上述化合物结构不同的腺苷A2受体拮抗剂，例如KW6002，也对糖尿病和糖尿病并发症的预防或治疗有效。在公式中，W是—CH2CH2—、—CH═CH—或—C≡C—; R1是：（在公式中，X是氢原子、羟基、低级烷基、低级烷氧基等；R5和R6相同或不同，分别代表氢原子、低级烷基、环烷基等）等；R2是氨基等，其可以被低级烷基等取代；R3是环烷基、可选取代的芳基等；R4是低级烷基等。
• Condensed imidazole compounds and a therapeutic agent for diabetes mellitus
  申请人：Asano Osamu

  公开号：US06841549B1

  公开（公告）日：2005-01-11

  The present invention provides a preventive or therapeutic agent for diabetes mellitus and diabetic complications, which is a new type based on an adenosine A2 receptor antagonist action. That is, it provides a novel condensed imidazole compound which has an adenosine A2 receptor antagonist action, is effective for preventing or treating diabetes mellitus and diabetic complications, and is represented by the formula (I); (wherein R 1 represents e.g. an amino group which may be substituted with an alkyl group; R 2 represents e.g. hydrogen atom, an alkyl group, a cycloalkyl group or an alkyl group, alkenyl group or alkynyl group which may be substituted with hydrox etc.; R 3 represents e.g. an optionally substituted alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, pyridinone group, pyrimidinone group or piperadinone group; Ar represents e.g. an optionally substituted aryl or heteroaryl group; and Q and W are the same as or different from each other and each represents N or CH), a pharmacologically acceptable salt or hydrates thereof.

  本发明提供了一种预防或治疗糖尿病和糖尿病并发症的药物，该药物是一种基于腺苷A2受体拮抗剂作用的新型药物。即，本发明提供了一种新型紧缩咪唑化合物，具有腺苷A2受体拮抗剂作用，对预防或治疗糖尿病和糖尿病并发症有效，其化学式表示为(I)；（其中，R1代表例如可用烷基取代的氨基基团；R2代表例如氢原子、烷基、环烷基或烷基、烯基或炔基，可用羟基等取代；R3代表例如可选取代的烷基、烯基、炔基、芳基、杂芳基、吡啶酮基、嘧啶酮基或哌啶酮基；Ar代表例如可选取代的芳基或杂芳基；Q和W相同或不同，分别代表N或CH），以及其药学上可接受的盐或水合物。