2-氨基-6-甲基-5-硝基-3H-嘧啶-4-酮 | 4214-85-1

• 物质功能分类: 医药中间体 - 杂环化合物 - 嘧啶类化合物
• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 中文名称: 2-氨基-6-甲基-5-硝基-3H-嘧啶-4-酮
• 中文别名: 2-氨基-4-羟基-6-甲基-5-硝基嘧啶
• 英文名称: 2-amino-6-methyl-5-nitropyrimidin-4-one
• 英文别名: 2-amino-6-methyl-5-nitro-4(3H)-oxopyrimidine；2-Amino-6-methyl-5-nitro-3H-pyrimidin-4-one；2-amino-4-methyl-5-nitro-1H-pyrimidin-6-one
• CAS: 4214-85-1
• 化学式: C₅H₆N₄O₃
• 分子量: 170.128
• InChiKey: PFTYCGMGNJVFIX-UHFFFAOYSA-N

物化性质

• 熔点：
  >300 °C
• 沸点：
  305.9±45.0 °C(Predicted)
• 密度：
  1.83±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  113
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933599090
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  5-硝基-6-甲基-脲嘧啶	5-nitro-6-methyluracil	16632-21-6	C5H5N3O4	171.112
  2-氯-6-甲基-5-硝基-4(1h)-嘧啶酮	2-Chlor-6-methyl-5-nitropyrimidin-4-ol	65224-66-0	C5H4ClN3O3	189.558

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	(E)-N,N-dimethyl-N'-(4-methyl-5-nitro-6-oxo-1,6-dihydropyrimidin-2-yl)formimidamide	914496-90-5	C8H11N5O3	225.207
  ——	2-[(dimethylamino)methyleneimino]-5-nitro-6-methyl-3H-pyrimidin-4-one	151587-54-1	C8H11N5O3	225.207
  N-(1,4-二氢-6-甲基-5-硝基-4-氧代-嘧啶-2-基)-乙酰胺	2-N-acetylamino-6-methyl-5-nitropyrimidin-4-one	299916-90-8	C7H8N4O4	212.165
  ——	2-pivaloylamino-5-nitro-6-methyluracil	1204824-43-0	C10H14N4O4	254.246
  2,5-二氨基-6-甲基-4(1H)-嘧啶酮	2,5-diamino-4-oxo-6-methyl pyrimidine	4214-86-2	C5H8N4O	140.145
  6-甲基-5-硝基-2,4-吡啶二胺	6-methyl-2,4-diamino-5-nitropyrimidine	2829-59-6	C5H7N5O2	169.143
  ——	N'-[4-[(E)-2-(dimethylamino)ethenyl]-1-methyl-5-nitro-6-oxopyrimidin-2-yl]-N,N-dimethylmethanimidamide	151587-59-6	C12H18N6O3	294.313

反应信息

• 作为反应物：
  描述：

  2-氨基-6-甲基-5-硝基-3H-嘧啶-4-酮 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 20.0~100.0 ℃ 、413.68 kPa 条件下， 反应 2.0h， 生成 N,N-dimethyl-N'-(4-oxo-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidin-2-yl)formamidine
  参考文献：
  名称：

  Novel Potent 5-HT_1F Receptor Agonists:  Structure−Activity Studies of a Series of Substituted N-[3-(1-Methyl-4-piperidinyl)-1H-pyrrolo[3,2-b]pyridin-5-yl]amides

  摘要：

  Compound 1a (LY334370), a selective 5-HT1F receptor agonist (SSOFRA), inhibited dural inflammation in the neurogenic plasma protein extravasation model of migraine and demonstrated clinical efficacy for the acute treatment of migraine. Although 1 was greater than 100-fold selective over both the 5-HT1B and 5-HT1D receptors, it exhibited appreciable 5-HT1A receptor affinity. Described here is the synthesis and evaluation of a series of pyrrolo[2,3-c]pyridine and pyrrolo[3,2-b]pyridine (2a and 3a) as well as pyrrolo[3,2-d]pyrimidine (4a) analogues of 1, compounds prepared in an effort to identify SSOFRAs with improved selectivity over other 5-HT1 receptor subtypes. The pyrrolo [3,2-b] pyridine analogue 3a showed high 5-HT1F receptor affinity but offered no improvement in selectivity compared to 1. However, the C-5 acetamide derivative, 3b, was greater than 100-fold selective over the 5-HT1A, 5-HT1B, and 5-HT1D receptors. SAR studies of this series determined that alkylamides in particular exhibited high selectivity for the 5-HT1F receptor. Replacement at C-5 with other substituents decreased affinity or selectivity. These SAR studies identified SSOFRAs that demonstrated oral activity in the neurogenic plasma protein extravasation model, a model indicative of antimigraine activity.

  DOI：

  10.1021/jm030020m
• 作为产物：
  描述：

  2-nitroamino-4(3H)-pyrimidinone 在 硫酸 作用下， 生成 2-氨基-6-甲基-5-硝基-3H-嘧啶-4-酮
  参考文献：
  名称：

  Sirakawa, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1953, vol. 73, p. 635,638

  摘要：

  DOI：

文献信息

• Addition of Lithiated 9-Deazapurine Derivatives to a Carbohydrate Cyclic Imine:  Convergent Synthesis of the Aza-<i>C</i>-nucleoside Immucillins
  作者：Gary B. Evans、Richard H. Furneaux、Tracy L. Hutchison、Hollis S. Kezar、Philip E. Morris,、Vern L. Schramm、Peter C. Tyler

  DOI：10.1021/jo0155613

  日期：2001.8.1

  Means have been developed for the synthesis and addition of 9-deaza-9-lithiopurine derivatives to the carbohydrate-derived cyclic imine 6 in facile convergent syntheses of biologically active aza-C-nucleosides.

  已经开发了在生物活性氮杂-C-核苷的容易会聚合成中将9-脱氮基-9-硫代嘌呤衍生物合成和添加至碳水化合物衍生的环亚胺6的方法。
• Process for preparing 2-pyrrolidinyl-1H-pyrrolo&lsqb;3,2-d&rsqb;pyrimidine inhibitors of nucleoside metabolism
  申请人：Industrial Research Limited

  公开号：US06693193B1

  公开（公告）日：2004-02-17

  A process of preparing a compound of the formula (I) wherein B is chosen from OH, NH2, NHR, H or halogen; D is chosen from OH, NH2, NHR, H halogen or SCH3; R is an optionally substituted alkyl, aralkyl or aryl group; and Z is selected from OH, hydrogen, halogen, hydroxy, SQ or OQ, Q is an optionally substituted all, aralkyl or aryl group; or a tautomer thereof; or a pharmaceutically acceptable salt thereof; or an ester thereof; or a prodrug thereof, which comprises reacting a compound of the formula (II)  with an anion produced by abstraction of the bromine or iodine atom from a compound of formula (XIX),  to form a compound of formula (XX) The compound of formula (XX) is N- and O-deprotected to obtain the compound of formula (I).

  将公式（I）的化合物制备过程翻译成中文： 其中B选择自OH、NH2、NHR、H或卤素；D选择自OH、NH2、NHR、H、卤素或SCH3；R是可选择取代的烷基、芳基烷基或芳基；Z选择自OH、氢、卤素、羟基、SQ或OQ，Q是可选择取代的烷基、芳基烷基或芳基；或其互变异构体；或其药学上可接受的盐；或其酯；或其前药，包括将公式（II）的化合物与通过从公式（XIX）的化合物中提取溴或碘原子而产生的负离子反应，形成公式（XX）的化合物。公式（XX）的化合物经N-和O去保护得到公式（I）的化合物。
• Synthesis of a Novel C-Nucleoside, 2-Amino-7-(2-deoxy-β- D-<i>erythro</i>-pentofuranosyl)-3H,5H-pyrrolo-[3,2-d]pyrimidin-4-one (2′-Deoxy-9-deazaguanosine)
  作者：Eric S. Gibson、Krystyna Lesiak、Kyoichi A. Watanabe、Lorraine J. Gudas、Krzysztof W. Pankiewicz

  DOI：10.1080/15257779908043082

  日期：1999.3

  A synthesis of the C-nucleoside, 2-amino-7-(2-deoxy-beta-D-erythro- pentofuranosyl)-3H,5H-pyrrolo[3,2-d]pyrimidin-4-one (9-deaza-2'-deoxyguanosine) was achieved starting from 2-amino-6-methyl-3H-pyrimidin-4-one (5) and methyl 2-deoxy-3,5-di-O-(p-nitrobenzoyl)-D-erythro-pento-furanoside (11). The anomeric configuration of the C-nucleoside was established by 1H NMR, NOEDS and ROESY. This C-nucleoside

  C-核苷，2-氨基-7-（2-脱氧-β-D-赤-呋喃呋喃糖基）-3H，5H-吡咯并[3,2-d]嘧啶-4-酮（9-脱氮-从2-氨基-6-甲基-3H-嘧啶-4-酮（5）和甲基2-脱氧-3,5-二-O-（对硝基苯甲酰基）-D-赤藓酸得到2'-脱氧鸟苷） -戊呋喃糖苷（11）。通过1 H NMR，NOEDS和ROESY建立C-核苷的异头构型。该C-核苷不抑制T细胞淋巴瘤细胞的生长。
• Diaryl-purines, azapurines and -deazapurines as non-nucleoside reverse transcriptase inhibitor for treatment of hiv
  申请人：Girardet Jean-Luc

  公开号：US20090124802A1

  公开（公告）日：2009-05-14

  This application concerns certain 2-phenylamino-6-aryl amino-, 6-aryloxy-, and 6-arylthio-purines, -azapurines and -deazapurines. These compounds are non-nucleoside reverse transcriptase inhibitors and have potential as anti-HIV treatment.

  这个应用涉及到一些2-苯基氨基-6-芳基氨基、6-芳氧基和6-芳基硫基嘌呤、-氮杂嘌呤和-脱氮杂嘌呤。这些化合物是非核苷类逆转录酶抑制剂，具有作为抗HIV治疗药物的潜力。
• Diaryl-purines, azapurines and -deazapurines as non-nucleoside reverse transcriptase inhibitor for treatment of HIV
  申请人：Ardea Biosciences, Inc.

  公开号：US08227601B2

  公开（公告）日：2012-07-24

  This application concerns certain 2-phenylamino-6-aryl amino-, 6-aryloxy-, and 6-arylthio-purines, -azapurines and -deazapurines. These compounds are non-nucleoside reverse transcriptase inhibitors and have potential as anti-HIV treatment.

  这个应用涉及到某些2-苯基氨基-6-芳基氨基，6-芳氧基和6-芳硫基嘌呤，嘌呤-氮杂嘧啶和去氮杂嘧啶。这些化合物是非核苷类逆转录酶抑制剂，具有作为抗HIV治疗的潜力。