2-acetamido-5-chloro-1,8-naphthyridine | 33007-28-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 2-acetamido-5-chloro-1,8-naphthyridine
• 英文别名: N-(5-chloro-1,8-naphthyridin-2-yl)acetamide
• CAS: 33007-28-2
• 化学式: C₁₀H₈ClN₃O
• 分子量: 221.646
• InChiKey: JXCYQXFZWFAGJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  54.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-acetamido-5-chloro-1,8-naphthyridine 在 硫酸 、 sodium nitrite 作用下， 反应 6.0h， 生成 5-氯-1,8-萘啶-2(1h)-酮
  参考文献：
  名称：

  Synthesis of 1,8-naphthyridine derivatives: potential antihypertensive agents – Part VIII

  摘要：

  A series of (ethoxycarbonylpiperazinyl)- and piperazinyl-1,8-naphthyridine derivatives, variously substituted, has been synthesized and pharmacologically investigated for anthihypertensive activity. Some of them exhibited a significant and prolonged decrease of the mean arterial pressure (MAP) on spontaneously hypertensive rats. On the basis of the pharmacological results, no structure-activity relationship can be deduced at this time. Moreover, the most active compound 4e, was investigated by means of in vitro pharmacological functional studies and in vivo, as a diuretic agent, to determine a possible mechanism of the antihypertensive activity, which results in a probably non-competitive antagonism against alpha(1), vascular adrenoceptors. This mechanism was also shown by the compounds 8 and 13. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(99)80099-3
• 作为产物：
  描述：

  2,6-二氨基吡啶 在 三乙胺 、 三氯氧磷 、 原甲酸三甲酯 作用下， 以 四氢呋喃 、 二苯醚 为溶剂， 反应 4.08h， 生成 2-acetamido-5-chloro-1,8-naphthyridine
  参考文献：
  名称：

  1,8-萘啶的合成及其在阴离子荧光化学传感器开发中的应用

  摘要：

  合成了两种 1,8-萘啶，发现在溶液中具有荧光。在存在 Cu +和 Cu 2+离子的情况下研究了这些化合物，并证实金属会导致它们的荧光发射猝灭，原因是萘啶和金属之间形成了络合物。在 DMSO-水混合物中进行置换试验，在复合物溶液中加入各种阴离子，观察到这些系统具有高选择性检测氰化物的能力。

  DOI：

  10.1007/s10895-012-1041-5

文献信息

• Quinoline derivatives inhibiting the effect of growth factors such as VEGF
  申请人：Zeneca Limited

  公开号：US06809097B1

  公开（公告）日：2004-10-26

  Compounds of the formula (I): wherein: R2 represents hydroxy, halogeno, C1-3alkyl, C1-3alkoxy, C1-3alkanoyloxy, trifluoromethyl, cyano, amino or nitro; n is an integer from 0 to 5; Z represents —O—, —NH—, —S— or —CH2—; G1 represents phenyl or a 5-10 membered heteroaromatic cyclic or bicyclic group; Y1, Y2, Y3 and Y4 each independently represents carbon or nitrogen; R1 represents fluoro or hydrogen; m is an integer from 1 to 3; R3 represents hydrogen, hydroxy, halogeno, cyano, nitro, trifluoromethyl, C1-3alkyl, —NR4R5 (wherein R4 and R5, can each be hydrogen or C1-3alkyl), or a group R6—X1— wherein X1 represents —CH2— or a heteroatom linker group and R6 is an alkyl, alkenyl or alkynyl chain optionally substituted by for example hydroxy, amino, nitro, alkyl, cycloalkyl, alkoxyalkyl, or an optionally substituted group selected from pyridone, phenyl and a heterocyclic ring, which alkyl, alkenyl or alkynyl chain may have a heteroatom linker group, or R6 is an optionally substituted group selected from pyridone, phenyl and a heterocyclic ring and salts thereof, in the manufacture of a medicament for use in the production of an antiangiogenic and/or vascular permeability reducing effect in warm-blooded animals such as humans, processes for the preparation of such derivatives, pharmaceutical compositions containing a compound of formula I or a pharmaceutically acceptable salt thereof as active ingredient and compounds of formula I. The compounds of formula I and the pharmaceutically acceptable salts thereof inhibit the effects of VEGF, a property of value in the treatment of a number of disease states including cancer and rheumatoid arthritis.

  公式(I)的化合物： 其中：R2代表羟基，卤素，C1-3烷基，C1-3烷氧基，C1-3烷酰氧基，三氟甲基，氰基，氨基或硝基；n是0到5之间的整数；Z代表—O—，—NH—，—S—或—CH2—；G1代表苯基或一个5-10员的杂芳环状或双环状基团；Y1、Y2、Y3和Y4各自独立代表碳或氮；R1代表氟或氢；m是1到3之间的整数；R3代表氢，羟基，卤素，氰基，硝基，三氟甲基，C1-3烷基，—NR4R5（其中R4和R5各自可以是氢或C1-3烷基），或一个R6—X1—基团，其中X1代表—CH2—或一个杂原子连接基团，R6是一个烷基、烯基或炔基链，该链可选地被例如羟基、氨基、硝基、烷基、环烷基、烷氧基烷基或一个可选地被取代的吡啶酮、苯基和杂环环取代，该烷基、烯基或炔基链可能含有一个杂原子连接基团，或者R6是一个可选地被取代的吡啶酮、苯基和杂环环，以及它们的盐，用于制造一种药物，用于在温血动物如人类中产生抗血管生成和/或降低血管通透性的效果，制备这类衍生物的过程，包含公式I的化合物或其药物可接受的盐作为活性成分的药物组合物，以及公式I的化合物。公式I的化合物及其药物可接受的盐抑制VEGF的效果，这一特性在治疗包括癌症和类风湿性关节炎在内的多种疾病状态中具有价值。
• 1,4-Dithiino(2,3-c)pyrrole derivatives
  申请人：Rhone-Poulenc S.A.

  公开号：US03948917A1

  公开（公告）日：1976-04-06

  New compounds of the formula: ##SPC1## Wherein A is a phenyl, pyridyl, pyridazinyl, 2-, 3- or 4-quinolyl or naphthyridinyl radical, or a said radical substituted by one or two atoms or radicals selected from halogen, alkyl, alkoxy cyano and nitro, R is alkyl, alkenyl or hydroxyalkyl, and n is zero or 1, possess pharmacological properties and are, in particular, active as tranquilisers, anti-convulsant agents, decontracturants and agents to produce hypnosis.

  新化合物的公式为：##SPC1## 其中A是苯基、吡啶基、吡嗪啉基、2-、3-或4-喹啉基或萘啉基基团，或者是一个被卤素、烷基、烷氧基、氰基和硝基中的一个或两个原子或基团取代的该基团，R是烷基、烯基或羟基烷基，n为0或1，具有药理学特性，特别是作为镇静剂、抗惊厥剂、解痉剂和催眠剂的活性。
• Synthesis of 1,8–Naphthyridines and Their Application in the Development of Anionic Fluorogenic Chemosensors
  作者：Celso R. Nicoleti、Diogo N. Garcia、Luiz E. da Silva、Iêda M. Begnini、Ricardo A. Rebelo、Antonio C. Joussef、Vanderlei G. Machado

  DOI：10.1007/s10895-012-1041-5

  日期：2012.7

  Two 1,8–naphthyridines were synthesized and found to be fluorescent in solution. These compounds were studied in the presence of Cu+ and Cu2+ ions and it was verified that the metal causes the quenching of their fluorescence emission, due to the formation of complexes between the naphthyridine and the metal. A displacement assay was carried out in a DMSO–water mixture with the addition of various anions

  合成了两种 1,8-萘啶，发现在溶液中具有荧光。在存在 Cu +和 Cu 2+离子的情况下研究了这些化合物，并证实金属会导致它们的荧光发射猝灭，原因是萘啶和金属之间形成了络合物。在 DMSO-水混合物中进行置换试验，在复合物溶液中加入各种阴离子，观察到这些系统具有高选择性检测氰化物的能力。
• Synthesis of Antimalarials. VI.¹ Synthesis of Certain 1,5- and 1,8-Naphthyridine Derivatives²
  作者：Joe T. Adams、Charles K. Bradsher、David S. Breslow、S. Thomas Amore、Charles R. Hauser

  DOI：10.1021/ja01211a064

  日期：1946.7
• QINOLINE DERIVATIVES INHIBITING THE EFFECT OF GROWTH FACTORS SUCH AS VEGF
  申请人：AstraZeneca AB

  公开号：EP0929526B1

  公开（公告）日：2005-07-27