2-chloro-6-phenyl-9H-purine | 73747-11-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 2-chloro-6-phenyl-9H-purine
• 英文别名: 2-chloro-6-phenylpurine；2-chloro-6-phenyl-7H-purine
• CAS: 73747-11-2
• 化学式: C₁₁H₇ClN₄
• 分子量: 230.656
• InChiKey: YJQPCOGQQFUKPV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-chloro-6-phenyl-9H-purine 在 potassium amide 作用下， 以 氨 为溶剂， 反应 70.0h， 以80%的产率得到2-amino-6-phenyl-9H-purine
  参考文献：
  名称：

  The SNANRORC mechanism. 27. Occurrence of the SNANRORC mechanism in the amination of 2-substituted purines with potassium amide in liquid ammonia

  摘要：

  DOI：

  10.1021/jo01303a004
• 作为产物：
  描述：

  2-chloro-4,5-diamino-6-phenylpyrimidine 、 alkaline earth salt of/the/ methylsulfuric acid 反应 3.0h， 以60%的产率得到2-chloro-6-phenyl-9H-purine
  参考文献：
  名称：

  The SNANRORC mechanism. 27. Occurrence of the SNANRORC mechanism in the amination of 2-substituted purines with potassium amide in liquid ammonia

  摘要：

  DOI：

  10.1021/jo01303a004

文献信息

• Aqueous-Phase Suzuki-Miyaura Cross-Coupling Reactions of Free Halopurine Bases
  作者：Michal Hocek、Petr Čapek、Milan Vrábel、Zbyněk Hasník、Radek Pohl

  DOI：10.1055/s-2006-950240

  日期：2006.10

  The Suzuki-Miyaura reaction of 9-unsubstituted 2-, 6-, and 8-halopurine bases with diverse aryl- and alkenylboronic acids in water-acetonitrile mixtures under microwave irradiation was used for the single-step synthesis of arylpurines. In most cases the product crystallized directly from the reaction mixture in high yields and good purity. The scope and limitations of these reactions were studied.

  通过水-乙腈混合物中微波辐照下，9-未取代的2-、6-和8-卤代嘌呤碱与多种芳基和烯基硼酸的Suzuki-Miyaura反应，实现了单步合成芳基嘌呤。在大多数情况下，产物以高产率直接从反应混合物中结晶，纯度良好。研究了这些反应的范围和局限性。
• Asymmetric Hydrogenation of α-Purine Nucleobase-Substituted Acrylates with Rhodium Diphosphine Complexes: Access to Tenofovir Analogues
  作者：Huan-Li Sun、Fei Chen、Ming-Sheng Xie、Hai-Ming Guo、Gui-Rong Qu、Yan-Mei He、Qing-Hua Fan

  DOI：10.1021/acs.orglett.6b00869

  日期：2016.5.6

  The first asymmetric hydrogenation of α-purine nucleobase-substituted α,β-unsaturated esters, catalyzed by a chiral rhodium (R)-Synphos catalyst, has been developed. A wide range of mono- and disubstituted acrylates were successfully hydrogenated under very mild conditions in high yields with good to excellent enantioselectivities (up to 99% ee). This method provides a convenient approach to the synthesis

  α嘌呤核碱基取代的α的第一不对称氢化，β -不饱和酯，通过手性铑催化（[R）-Synphos催化剂，已经研制成功。在非常温和的条件下，以高收率和良好至优异的对映选择性（高达99％ee）成功地氢化了各种单取代和二取代的丙烯酸酯。该方法为合成新型光学纯的无环核苷和替诺福韦类似物提供了便利的方法。
• Purine Compunds as HSP90 Protein Inhibitors for the Treatment of Cancer
  申请人：BROUGH Paul Andrew

  公开号：US20090181989A1

  公开（公告）日：2009-07-16

  Compounds of formula (I) are inhibitors of HSP90, and of utility in the treatment of, for example, cancers: wherein ring A is an aryl or heteroaryl ring or ring system; R 1 is hydrogen, fluoro, chloro, bromo, or a radical of formula (IA): —X-Alk 1 -(Z) m -(Alk 2 ) n -Q (IA) wherein X is a bond, —O—, —S— —S(O)—, —SO 2 —, or —NH—, Z is —O—, —S—, —(C═O)—, —(C═S)—, —S(O)—, —SO 2 —, —NR A , or, in either orientation —C(═O)O—, —C(═O)NR A , —C(═S)NR A —, —SO 2 NR A —, —NR A C(═O)—, or —NR A SO 2 — wherein R A is hydrogen or C 1 -C 6 alkyl in which one or more hydrogens is optionally substituted by fluorine; Alk 1 and Alk 2 are optionally substituted divalent C 1 -C 3 alkylene or C 2 -C 3 alkenylene radicals, m and n are independently 0 or 1, and Q is hydrogen or an optionally substituted carbocyclic or heterocyclic radical; R 2 is cyano (—CN), fluoro, chloro, bromo, methyl, ethyl, —OH, —CH 2 OH, —C(═O)NH 2 , —C(═O)H, —C(═O)CH 3 , or —NH 2 ; R 3 and R 4 are independently selected from hydrogen, fluoro, chloro, bromo, cyano (—CN), C 1 -C 3 alkyl optionally substituted with one or more fluorine substituents, C 1 -C 3 alkoxy optionally substituted with one or more fluorine substituents, —CH═CH 2 , —C≡CH, cyclopropyl and —NH 2 , or R 3 and R 4 together represent a carbocyclic or heterocyclic ring fused to ring A, or methylenedioxy (—OCH 2 O—) or ethylenedioxy (—OCH 2 CH 2 O—) in either of which one or more hydrogens are optionally replaced by fluorine; S 1 is hydrogen, or a substituent as defined in the specification.

  式(I)的化合物是HSP90的抑制剂，在治疗癌症等方面有用：其中环A是芳基或杂芳基环或环系；R1是氢，氟，氯，溴或式(IA)的基团：—X-Alk1-(Z)m-(Alk2)n-Q (IA)，其中X是键，—O—，—S—，—S(O)—，—SO2—或—NH—，Z是—O—，—S—，—(C═O)—，—(C═S)—，—S(O)—，—SO2—，—NRA或，以任何方向为定向，—C(═O)O—，—C(═O)NRA，—C(═S)NRA—，—SO2NRA—，—NRAC(═O)—或—NRASO2—，其中RA是氢或C1-C6烷基，其中一个或多个氢原子可以被氟代取代；Alk1和Alk2是可选取代的二价C1-C3烷基或C2-C3烯基基团，m和n独立地为0或1，Q是氢或可选取代的碳环或杂环基团；R2是氰基(—CN)，氟，氯，溴，甲基，乙基，—OH，—CH2OH，—C(═O)NH2，—C(═O)H，—C(═O)CH3或—NH2；R3和R4独立选择自氢，氟，氯，溴，氰基(—CN)，C1-C3烷基，其中一个或多个氟代取代，C1-C3烷氧基，其中一个或多个氟代取代，—CH═CH2，—C≡CH，环丙基和—NH2，或R3和R4共同代表与环A融合的碳环或杂环，或者是甲二氧基(—OCH2O—)或乙二氧基(—OCH2CH2O—)，其中一个或多个氢原子可以被氟代取代；S1是氢或规范中定义的取代基。
• Ectonucleotidase inhibitors and methods of use thereof
  申请人：Calithera Biosciences, Inc.

  公开号：US11078228B2

  公开（公告）日：2021-08-03

  The invention relates to novel heterocyclic compounds and pharmaceutical preparations thereof. The invention further relates to methods of treating or preventing cancer using the novel heterocyclic compounds of the invention.

  本发明涉及新型杂环化合物及其药物制剂。本发明还涉及使用本发明的新型杂环化合物治疗或预防癌症的方法。
• WO2019246403A5
  申请人：——

  公开号：WO2019246403A5

  公开（公告）日：2022-05-16