4-氯-2-氟苄胺盐酸盐 | 202982-63-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-氯-2-氟苄胺盐酸盐
• 英文名称: (4-chloro-2-fluorophenyl)methanamine hydrochloride
• 英文别名: 4-chloro-2-fluorobenzylamine hydrochloride；(4-Chloro-2-fluorophenyl)methylazanium;chloride
• CAS: 202982-63-6
• 化学式: C₇H₇ClFN*ClH
• mdl: MFCD00143286
• 分子量: 196.052
• InChiKey: DFRJZBWKVAXYRV-UHFFFAOYSA-N

物化性质

• 熔点：
  236-241 °C
• 密度：
  1.2175 (estimate)
• 稳定性/保质期：

  避氧化物

计算性质

• 辛醇/水分配系数(LogP)：
  1.85
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  26
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xn,C
• 危险类别码：
  R36/37/38
• 海关编码：
  2921499090
• 安全说明：
  S26,S36/37/39
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  4-氯-2-氟苄胺盐酸盐 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 3-amino-5-((4-chloro-2-fluorobenzyl)amino)-1H-pyrazole-4-carbonitrile
  参考文献：
  名称：

  The Discovery of in Vivo Active Mitochondrial Branched-Chain Aminotransferase (BCATm) Inhibitors by Hybridizing Fragment and HTS Hits

  摘要：

  The hybridization of hits, identified by complementary fragment and high throughput screens, enabled the discovery of the first series of potent inhibitors of mitochondrial branched-chain aminotransferase (BCATm) based on a 2-benzylamino-pyrazolo[1,5-a]-pyrimidinone-3-carbonitrile template. Structure-guided growth enabled rapid optimization of potency with maintenance of ligand efficiency, while the focus on physicochemical properties delivered compounds with excellent pharmacokinetic exposure that enabled a proof of concept experiment in mice. Oral administration of 2-((4-chloro-2,6-difluorobenzyl)amino)-7-oxo-5-propyl-4,7-dihydropyrazolo[1,5-a]-pyrimidine-3-carbonitrile 61 significantly raised the circulating levels of the branched-chain amino acids leucine, isoleucine, and valine in this acute study.

  DOI：

  10.1021/acs.jmedchem.5b00313
• 作为产物：
  描述：

  N-(4-氯-2-氟苄基)邻苯二甲酰亚胺 在 肼 、 盐酸 作用下， 以 甲醇 、 水 、 乙腈 为溶剂， 反应 2.5h， 生成 4-氯-2-氟苄胺盐酸盐
  参考文献：
  名称：

  EP1577290

  摘要：

  公开号：

文献信息

• Amide compound and method of controlling plant disease with the same
  申请人：Sakaguchi Hiroshi

  公开号：US20060122065A1

  公开（公告）日：2006-06-08

  A amid compound of the formula (1): wherein, in the formula, R 51 represents a halogen atom, a C1-C6 alkyl group and the like; R 52 represents a hydrogen atom, a halogen atom, a C1-C6 alkyl group and the like; R 53 represents a halogen atom and the like; R 56 represents a halogen atom and the like; R 57 represents a hydrogen atom and the like; R 58 and R 59 independently represent a hydrogen atom, a C1-C3 alkyl group and the like; R 60 represents a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C3-C4 alkenyl group, or a C3-C6 alkynyl group; R 61 represents a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C3-C4 alkenyl group or a C3-C6 alkynyl group or a C2-C4 cyanoalkyl group; R 62 , R 63 and R 64 represent a hydrogen atom, a halogen atom and the like; X represents a oxygen atom or a sulfur atom; has an excellent activity against plant diseases.

  一种化合物的公式（1）：其中，在公式中，R51代表卤素原子，C1-C6烷基等；R52代表氢原子，卤素原子，C1-C6烷基等；R53代表卤素原子等；R56代表卤素原子等；R57代表氢原子等；R58和R59分别独立地代表氢原子，C1-C3烷基等；R60代表C1-C4烷基，C1-C4卤代烷基，C3-C4烯基或C3-C6炔基；R61代表C1-C4烷基，C1-C4卤代烷基，C3-C4烯基或C3-C6炔基或C2-C4氰基烷基；R62，R63和R64代表氢原子，卤素原子等；X代表氧原子或硫原子；具有出色的植物病害活性。
• AMIDE COMPOUND AND METHOD OF CONTROLLING PLANT DISEASE WITH THE SAME
  申请人：Sumitomo Chemical Company, Limited

  公开号：EP1577290A1

  公开（公告）日：2005-09-21

  A amid compound of the formula (1): wherein, in the formula, R51 represents a halogen atom, a C1-C6 alkyl group and the like; R52 represents a hydrogen atom, a halogen atom, a C1-C6 alkyl group and the like; R53 represents a halogen atom and the like; R56 represents a halogen atom and the like; R57 represents a hydrogen atom and the like; R58 and R59 independently represent a hydrogen atom, a C1-C3 alkyl group and the like; R60 represents a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C3-C4 alkenyl group, or a C3-C6 alkynyl group; R61 represents a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C3-C4 alkenyl group or a C3-C6 alkynyl group or a C2-C4 cyanoalkyl group; R62, R63 and R64 represent a hydrogen atom, a halogen atom and the like; X represents a oxygen atom or a sulfur atom; has an excellent activity against plant diseases.

  一种式（1）的酰胺化合物： 式中 R51 代表卤素原子、C1-C6 烷基等； R52 代表氢原子、卤素原子、C1-C6 烷基等； R53 代表卤素原子等； R56 代表卤原子等； R57 代表氢原子等； R58 和 R59 独立地代表氢原子、C1-C3 烷基等； R60 代表 C1-C4 烷基、C1-C4 卤代烷基、C3-C4 烯基或 C3-C6 烷炔基；R61代表 C1-C4 烷基、C1-C4 卤代烷基、C3-C4 烯基或 C3-C6 炔基或 C2-C4 氰烷基；R62、R63 和 R64 代表氢原子、卤素原子等；X 代表氧原子或硫原子； 对植物病害具有极佳的活性。
• Novel, Highly Potent Aldose Reductase Inhibitors:  (<i>R</i>)-(−)-2-(4-Bromo-2-fluorobenzyl)-1,2,3,4-tetrahydropyrrolo[1,2-<i>a</i>]pyrazine- 4-spiro-3‘-pyrrolidine-1,2‘,3,5‘-tetrone (AS-3201) and Its Congeners
  作者：Toshiyuki Negoro、Makoto Murata、Shozo Ueda、Buichi Fujitani、Yoshiyuki Ono、Akemi Kuromiya、Masanobu Komiya、Kenji Suzuki、Jun-ichi Matsumoto

  DOI：10.1021/jm9802968

  日期：1998.10.1

  A series of novel tetrahydropyrrolo[1,2-a]pyrazine derivatives were synthesized and evaluated as aldose reductase inhibitors (ARIs) on the basis of their abilities to inhibit porcine lens aldose reductase (AR) in vitro and to inhibit sorbitol accumulation in the sciatic nerve of streptozotocin-induced diabetic rats in vivo. Of these compounds, spirosuccinimide-fused tetrahydropyrrolo[1,2-a]pyrazine-1,3-dione derivatives showed significantly potent AR inhibitory activity. In the in vivo activity of these derivatives, 2-(4-bromo-2-fluorobenzyl)-1,2,3,4-tetrahydropyrrolo- [1,2-a][1,2a]pyrazine-4-spiro-3'-pyrrolidine-1,2',3,5'-tetrone (23t) (SX-3030) showed the best oral activity. The enantiomers of 23t were synthesized, and the biological activities were evaluated. It was found that AR inhibitory activity resides in the (-)-enantiomer 43 (AS-3201), which was 10 times more potent in inhibition of the AR (IC50 = 1.5 x 10(-8) M) and 500 times more potent in the in vivo activity (ED50 = 0.18 mg/kg/day for 5 days) than the corresponding (+)enantiomer 44 (SX-3202): From these results, AS-3201 was selected as the candidate for clinical development. The absolute configuration of AS-3201 was also established to be (R)-form by single-crystal X-ray analysis. In this article we report the preparation and structure-activity relationship (SAR) of tetrahydropyrrolopyrazine derivatives including a novel ARI, AS-3201.
• Exploring the Role of <i>N</i>⁶-Substituents in Potent Dual Acting 5′-<i>C</i>-Ethyltetrazolyladenosine Derivatives: Synthesis, Binding, Functional Assays, and Antinociceptive Effects in Mice
  作者：Riccardo Petrelli、Mirko Scortichini、Sonja Kachler、Serena Boccella、Carmen Cerchia、Ilaria Torquati、Fabio Del Bello、Daniela Salvemini、Ettore Novellino、Livio Luongo、Sabatino Maione、Kenneth A. Jacobson、Antonio Lavecchia、Karl-Norbert Klotz、Loredana Cappellacci

  DOI：10.1021/acs.jmedchem.7b00291

  日期：2017.5.25

  Structural determinants of affinity of N-6-substituted-5'-C-(ethyltetrazol-2-yl)adenosine and 2-chloroadenosine derivatives at adenosine receptor (AR) subtypes were studied with binding and molecular modeling. Small N-6-cycloalkyl and 3-halobenzyl groups furnished potent dual acting A(1)AR agonists and A(3)AR antagonists. 4 was the most potent dual acting human (h) AFAR agonist (K-i = 0.45 nM) and A(3)AR antagonist (K-i = 0.31 nM) and highly selective versus A(2A); 11 and 26 were most potent at both h and rat (r) A(3)AR. All N-6-substituted-5'-C-(ethyltetrazol-2-yl)adenosine derivatives proved to be antagonists at hA(3)AR but agonists at the rA(3)AR. Analgesia of 11, 22, and 26 was evaluated in the mouse formalin test (A(3)AR antagonist blocked and A(3)AR agonist strongly potentiated). N-6-Methyl-5'-C-(ethyltetrazol-2-yl)adenosine (22) was most potent, inhibiting both phases, as observed combining AFAR and A(3)AR agonists. This study demonstrated for the first time the advantages of a single molecule activating two AR pathways both leading to benefit in this acute pain model.