3-溴-1H-吡唑并[3,4-d]嘧啶-4,6-二胺 | 144750-82-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡唑并嘧啶类
• 中文名称: 3-溴-1H-吡唑并[3,4-d]嘧啶-4,6-二胺
• 中文别名: 1H-吡唑并[3,4-d]嘧啶-4,6-二胺,3-溴-
• 英文名称: 2,4-Diamino-5-bromo-7H-pyrazolo<3,4-d>pyrimidine
• 英文别名: 3-bromo-1H-pyrazolo[3,4-d]pyrimidine-4,6-diamine；3-bromo-2H-pyrazolo[3,4-d]pyrimidine-4,6-diamine
• CAS: 144750-82-3
• 化学式: C₅H₅BrN₆
• 分子量: 229.039
• InChiKey: FVOVQYNWRQMJNK-UHFFFAOYSA-N

物化性质

• 沸点：
  341.4±52.0 °C(Predicted)
• 密度：
  2.82±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  107
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-溴-1H-吡唑并[3,4-d]嘧啶-4,6-二胺 在 三氟化硼乙醚 吡啶 、 甲醇 、 sodium methylate 、 silver nitrate 作用下， 以 四氢呋喃 、 甲醇 、 硝基甲烷 为溶剂， 生成 N-[1-[5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-tetrahydro-furan-2-yl]-3-bromo-4-(dibutylamino-methyleneamino)-1H-pyrazolo[3,4-d]pyrimidin-6-yl]-formamide
  参考文献：
  名称：

  7-SUBSTITUTED 8-AZA-7-DEAZAPURINES AND 2,8-DIAZA-7-DEAZA-PURINES: SYNTHESIS OF NUCLEOSIDES AND OLIGONUCLEOTIDES

  摘要：

  7-Substituted 8-aza-7-deazaadenosines la-e were synthesized by Sonogashira cross coupling from the corresponding 7-iodo nucleoside in 36- 79% yields. Starting from 7-bromo (or 7-iodo)-8-aza- 7-deazaadenine, 2a,b were obtained by acid-catalyzed glycosylation followed by deprotection in 53 and 35% yields, respectively. Compounds 2b was applied to cross coupling reaction to give 2c-d in 34-95% yield. Compounds 2a and 4b were further transformed to the phosphoramidites 5 and 6b in 9 and 49% overall yields, which were incorporated into oligonucleotides.

  DOI：

  10.1081/ncn-200059218
• 作为产物：
  描述：

  1H-吡唑并[3,4-D]嘧啶-4,6-二胺 在 溴 作用下， 以 水 为溶剂， 反应 1.0h， 以62%的产率得到3-溴-1H-吡唑并[3,4-d]嘧啶-4,6-二胺
  参考文献：
  名称：

  与2-氨基腺苷和异鸟苷有关的吡唑并[3,4-d]嘧啶核糖核苷：合成，脱氨基和互变异构。

  摘要：

  描述了与2-氨基腺苷和异鸟苷相关的8-氮杂-7-脱氮嘌呤（吡唑并[3,4-d]嘧啶）核糖核苷的合成和性质。在BF（3）存在下，将1-氮-乙酰基2,3,5-三-O-苯甲酰基-β-D-呋喃呋喃糖与8-氮杂7-脱氮嘌呤-2,6-二胺5糖基化。 ）x Et（2）O作为催化剂，得到N（8）异构体14（73％）和痕量的N（9）异构体13a（4.8％）。在相同的反应条件下，7-卤代8-氮杂-7-脱氮嘌呤-2,6-二胺6-8提供了热力学上更稳定的N（9）核苷13b-d作为唯一产物（53-70％）。因此，位置7的卤素将糖基化作用从N（8）转移到N（9）。通过2-氨基的重氮化将8-氮杂-7-脱氮嘌呤-4，6-二胺核糖核苷1a-d转化为异鸟苷衍生物3a-d。尽管化合物1a b。在7位（酶结合位点）不含氮，它们被腺苷脱氨酶脱氨；但是，它们的脱氨速度比相关嘌呤的速度要慢得多。pK（a）值表明，将7个非功能化核苷1a（pK（a）5

  DOI：

  10.1039/b708736e

文献信息

• [EN] PYRROLOTRIAZINONE DERIVATIVES AS PI3K INHIBITORS<br/>[FR] DÉRIVÉS DE PYRROLOTRIAZINONE EN TANT QU'INHIBITEURS DES PI3K
  申请人：ALMIRALL SA

  公开号：WO2014060431A1

  公开（公告）日：2014-04-24

  New pyrrolotriazinone derivatives having the chemical structure of formula (I) are disclosed; as well as process for their preparation, pharmaceutical compositions comprising them and their use in therapy as inhibitors of Phosphoinositide 3-Kinases (PI3Ks).

  披露了具有公式(I)化学结构的新型吡咯三嗪酮衍生物；以及它们的制备方法，包含它们的药物组合物以及它们作为磷脂酰肌醇3-激酶（PI3Ks）抑制剂在治疗中的用途。
• Synthesis of pyrazolo 3,4-pyrimidine analogues of the potent agent N-4-2-2-amino-4 3-oxo-7-pyrrolo 2,3-pyrimidin-5-yl ethylbenzoyl-L-glutamic acid (LY231514)
  作者：Edward C. Taylor、Hemantkumar H. Patel

  DOI：10.1016/s0040-4020(01)80479-8

  日期：1992.1

  Several pyrazolo[3,4-d]pyrimidine analogues of the potent antitumor agent N-4-12-(2-amino-4(3H)-oxo-7H-pyrrolo [2,3-d]pyrimidin-5-yl)ethyl]benzoyl}-L-glutamic acid (LY231514, 5) have been prepared. A principal synthetic step proved to be a palladium-catalyzed C-C coupling of the 5-halo-substituted pyrazolo[3,4-d]pyrimidines 12-15 with dimethyl 4-ethynylbenzoyl-L-glutamate (16). An additional pyrazolo[3,4-d]pyrimidine analogue of 5 possessing an isofolic acid bridge unit (-NHCH2-) was prepared by reductive alkylation of diethyl 4-formylbenzoyl-L-glutamate (31) with 2-methyl-5-amino-4(3H)-oxo-7H-pyrazolo[3,4-d]pyrimidine (30). Only compound 26 proved to have in vitro cell growth inhibitory activity.
• 7-SUBSTITUTED 8-AZA-7-DEAZAPURINES AND 2,8-DIAZA-7-DEAZA-PURINES: SYNTHESIS OF NUCLEOSIDES AND OLIGONUCLEOTIDES
  作者：Wenqing Lin、Kuiying Xu、Frank Seela

  DOI：10.1081/ncn-200059218

  日期：2005.4.1

  7-Substituted 8-aza-7-deazaadenosines la-e were synthesized by Sonogashira cross coupling from the corresponding 7-iodo nucleoside in 36- 79% yields. Starting from 7-bromo (or 7-iodo)-8-aza- 7-deazaadenine, 2a,b were obtained by acid-catalyzed glycosylation followed by deprotection in 53 and 35% yields, respectively. Compounds 2b was applied to cross coupling reaction to give 2c-d in 34-95% yield. Compounds 2a and 4b were further transformed to the phosphoramidites 5 and 6b in 9 and 49% overall yields, which were incorporated into oligonucleotides.
• Pyrazolo[3,4-d]pyrimidine ribonucleosides related to 2-aminoadenosine and isoguanosine: synthesis, deamination and tautomerism
  作者：Frank Seela、Kuiying Xu

  DOI：10.1039/b708736e

  日期：——

  than that of the related purines. The pK(a) values indicate that the 7-non-functionalized nucleosides 1a (pK(a) 5.8) and 15 (pK(a) 6.4) are possibly protonated in neutral conditions when incorporated into RNA. The nucleosides 3a-d exist predominantly in the keto (lactam) form with K(TAUT) (keto/enol) values of 400-1200 compared to 10(3)-10(4) for pyrrolo[2,3-d]pyrimidine isoguanosine derivatives 4a-c

  描述了与2-氨基腺苷和异鸟苷相关的8-氮杂-7-脱氮嘌呤（吡唑并[3,4-d]嘧啶）核糖核苷的合成和性质。在BF（3）存在下，将1-氮-乙酰基2,3,5-三-O-苯甲酰基-β-D-呋喃呋喃糖与8-氮杂7-脱氮嘌呤-2,6-二胺5糖基化。 ）x Et（2）O作为催化剂，得到N（8）异构体14（73％）和痕量的N（9）异构体13a（4.8％）。在相同的反应条件下，7-卤代8-氮杂-7-脱氮嘌呤-2,6-二胺6-8提供了热力学上更稳定的N（9）核苷13b-d作为唯一产物（53-70％）。因此，位置7的卤素将糖基化作用从N（8）转移到N（9）。通过2-氨基的重氮化将8-氮杂-7-脱氮嘌呤-4，6-二胺核糖核苷1a-d转化为异鸟苷衍生物3a-d。尽管化合物1a b。在7位（酶结合位点）不含氮，它们被腺苷脱氨酶脱氨；但是，它们的脱氨速度比相关嘌呤的速度要慢得多。pK（a）值表明，将7个非功能化核苷1a（pK（a）5