2-氯-3,5-二碘-4-吡啶胺 | 1171919-00-8

• 物质功能分类: 医药中间体 - 吡啶类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 2-氯-3,5-二碘-4-吡啶胺
• 英文名称: 2-chloro-3,5-diiodopyridin-4-amine
• CAS: 1171919-00-8
• 化学式: C₅H₃ClI₂N₂
• 分子量: 380.354
• InChiKey: ADBYPUPWCVKWCP-UHFFFAOYSA-N

物化性质

• 熔点：
  158-159°

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  38.9
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933399090
• 包装等级：
  III
• 危险类别：
  6.1
• 危险性防范说明：
  P261,P264,P270,P271,P280,P302+P352,P304+P340,P310,P330,P361,P403+P233,P405,P501
• 危险品运输编号：
  2811
• 危险性描述：
  H301,H311,H331

反应信息

• 作为产物：
  描述：

  2-氯-4-氨基吡啶 在 sodium acetate 、 一氯化碘 、 溶剂黄146 作用下， 反应 2.0h， 以45%的产率得到2-氯-5-碘-4-吡啶胺
  参考文献：
  名称：

  Discovery of N-[5-(6-Chloro-3-cyano-1-methyl-1H-indol-2-yl)-pyridin-3-ylmethyl]-ethanesulfonamide, a Cortisol-Sparing CYP11B2 Inhibitor that Lowers Aldosterone in Human Subjects

  摘要：

  Human clinical studies conducted with LCI699 established aldosterone synthase (CYP11B2) inhibition as a promising novel mechanism to lower arterial blood pressure. However, LCI699's low CYP11B1/CYP11B2 selectivity resulted in blunting of adrenocorticotropic hormone-stimulated cortisol secretion. This property of LCI699 prompted its development in Cushing's disease, but limited more extensive clinical studies in hypertensive populations, and provided an impetus for the search for cortisol-sparing CYP11B2 inhibitors. This paper summarizes the discovery, pharmacokinetics, and pharmacodynamic data in predinical species and human subjects of the selective CYP11B2 inhibitor 8.

  DOI：

  10.1021/acs.jmedchem.5b01545

文献信息

• Palladium-Catalyzed Synthesis of 2,3-Disubstituted 5-Azaindoles via Heteroannulation Reaction and of 2-Substituted 5-Azaindoles through Domino Sila-Sonogashira/5-Endo Cyclization
  作者：Marion Livecchi、Géraldine Calvet、Frédéric Schmidt

  DOI：10.1021/jo300481s

  日期：2012.6.1

  A general and efficient procedure for the synthesis of 2,3-disubstituted 5-azaindoles through the palladium-catalyzed heteroannulation of 4-acetamido-3-iodopyridines and diaryl-, dialkyl-, or arylalkylalkynes is described along with a study of the reaction regioselectivity. The preparation of 2-monosubstituted 5-azaindoles via sila-Sonogashira/5-endo cyclization is also reported. These methods allowed

  描述了通过钯催化的4-乙酰氨基-3-碘吡啶和二芳基，二烷基或芳基烷基炔烃的异环合成2,3-二取代的5-氮杂吲哚的一般有效方法，以及对反应区域选择性的研究。 。还报道了通过sila-Sonogashira / 5-endo环化制备2-单取代的5-氮杂吲哚。这些方法使我们能够以高收率制备36种不同取代的5-氮杂吲哚。
• New polyfunctional imidazo[4,5-C]pyridine motifs: Synthesis, crystal studies, docking studies and antimicrobial evaluation
  作者：Gilish Jose、T.H. Suresha Kumara、Gopalpur Nagendrappa、H.B.V. Sowmya、Jerry P. Jasinski、Sean P. Millikan、N. Chandrika、Sunil S. More、B.G. Harish

  DOI：10.1016/j.ejmech.2014.03.019

  日期：2014.4

  New antimicrobial agents, imidazo[4,5-c]pyridine derivatives have been synthesized. We have developed a new synthetic protocol for the final reaction, an efficient microwave-assisted synthesis of imidazo[4,5-c]pyridines from substituted 3,4-diaminopyridine and carboxylic acids in presence of DBU mediated by T3P. The chemical structures of the new compounds were characterized by IR, 1H NMR, 13C NMR

  已经合成了新的抗菌剂，咪唑并[4,5- c ]吡啶衍生物。我们已经开发出一种用于最终反应的新合成方案，即在T3P介导的DBU存在下，由取代的3,4-二氨基吡啶和羧酸高效微波辅助合成咪唑并[4,5-c]吡啶。通过IR，1 H NMR，13 C NMR，质谱分析和元素分析对新化合物的化学结构进行了表征。另外，还已经记录了化合物9c的单晶X射线衍射。在体外的化合物的抗微生物活性对各种革兰氏阴性，革兰氏阳性细菌和真菌进行的。在经过测试的化合物9c中，9e，9g，9k和9l显示出有希望的抗菌活性。进行了GlcN-6-P合酶与新合成化合物的分子对接。
• Synthesis, molecular docking, antimycobacterial and antimicrobial evaluation of new pyrrolo[3,2- c ]pyridine Mannich bases
  作者：Gilish Jose、Tholappanavara H. Suresha Kumara、Haliwana B.V. Sowmya、Dharmarajan Sriram、Tayur N. Guru Row、Amar A. Hosamani、Sunil S. More、Bhavya Janardhan、B.G. Harish、Sandeep Telkar、Yalegara Siddappa Ravikumar

  DOI：10.1016/j.ejmech.2017.03.015

  日期：2017.5

  using MABA. Compounds 7r, 7t, and 7u were showed good antitubercular activity against Mtb (MIC ≥6.25 μg/mL). Among the tested compounds, 1-((4-chloro-2-(cyclohexylmethyl)-1H-pyrrolo[3,2-c]pyridin-3-yl)methyl)piperidine-3-carboxamide (7t) was showed excellent antimycobacterial activity against Mtb (MIC <0.78 μg/mL) and low cytotoxicity against the HEK-293T cell line (SI >>25). Molecular docking of the

  在本报告中，我们描述了一系列新的吡咯并[3,2-c]吡啶曼尼希碱（7a-v）的合成和生物学评估。曼尼希碱是通过吡咯并[3,2-c]吡啶骨架（6a-c）与仲胺和过量的甲醛溶液在AcOH中一锅三组分缩合获得的。化合物的化学结构通过1 H NMR，13 C NMR，LC / MS和元素分析进行​​表征。已记录化合物7k（[C23H29ClN4] +2，H2O）的单晶X射线衍射。使用琼脂扩散法和肉汤微量稀释法评估了化合物对各种细菌和真菌菌株的体外抗菌活性。化合物7e，7f，7r，7t和7u对金黄色葡萄球菌，弯曲弯曲杆菌，产气链球菌和变形链球菌显示出良好的革兰氏阳性抗菌活性。此外，使用MABA评估了对结核分枝杆菌H37Rv（ATCC 27294）的体外抗分枝杆菌活性。化合物7r，7t和7u对Mtb（MIC≥6.25μg/ mL）表现出良好的抗结核活性。在测试的化合物中，1-（（4-氯-2-（环己基甲基）-1H-吡咯并[3
• Synthesis, crystal structure, molecular docking and antimicrobial evaluation of new pyrrolo[3,2-c]pyridine derivatives
  作者：Gilish Jose、T.H. Suresha Kumara、Gopalpur Nagendrappa、H.B.V. Sowmya、Jerry P. Jasinski、Sean P. Millikan、Sunil S. More、Bhavya Janardhan、B.G. Harish、N. Chandrika

  DOI：10.1016/j.molstruc.2014.10.006

  日期：2015.2

  New antibacterial agents, pyrrolo[3,2-c]pyridine derivatives have been designed and synthesized. The structural considerations of the designed molecules were further supported by the docking study with GlcN-6-P synthase. The chemical structures of the new compounds were characterized by NMR, mass spectral analysis and elemental analysis. Single crystals of two compounds, C13H15N2Cl [6a] and C21H24N3OCl, CH4O [7c] were obtained allowing for structural analysis. [C13H15N2Cl] monoclinic, P2(1)/c, a = 9.9763(6) angstrom, b = 9.6777(6) angstrom, c = 13.3002(9) angstrom, beta = 106.459(7)degrees, V = 1231.47(14) angstrom(3), Z = 4, T = 173(2) K, mu(Cu K alpha) = 2.522 mm(-1), D-calc = 1.266 g/mm(3), 7124 reflections, 2404 unique (R-int= 0.0381), R-1 = 0.0420 (I > 2 sigma(I)) and wR(2) = 0.1254 (all data). [C21H24N3OCl, CH4O] triclinic, P-1, a = 10.1478(7) angstrom, b = 12.0945(8) angstrom, c = 18.3244(10) angstrom, alpha = 104.369(5)degrees, beta = 90.766(5)degrees, gamma = 99.23 5(6)degrees, V = 2147.1(2) angstrom(3), Z = 4, T = 1 73(2) K, mu(CU K alpha) = 1.744 mm(-1), D-calc = 1.243 g/mm(3), 14238 reflections, 8297 unique (R-int = 0.0330), R-1= 0.0578 (I> 2 sigma(1)) and wR(2) = 0.1773 (all data). The in vitro antimicrobial activities of the compounds were conducted against various Gram-negative, Gram-positive bacteria and fungi. Amongst the tested compounds 7e displayed promising antibacterial activity against Gram-positive bacteria Bacillus flexus compared to antibiotic Amoxicillin. (C) 2014 Elsevier B.V. All rights reserved.